diff --git a/.claude/settings.json b/.claude/settings.json
index ac6b69b143..416bb2617f 100644
--- a/.claude/settings.json
+++ b/.claude/settings.json
@@ -27,7 +27,14 @@
       "WebFetch(domain:docs.sentry.io)",
       "WebFetch(domain:develop.sentry.dev)",
       "Bash(grep:*)",
-      "Bash(mv:*)"
+      "Bash(mv:*)",
+      "Bash(source .venv/bin/activate)",
+      "Bash(source tox.venv/bin/activate:*)",
+      "Bash(tox:*)",
+      "Bash(tox.venv/bin/tox:*)",
+      "Bash(.tox/*/bin/python:*)",
+      "Bash(.tox/*/bin/pytest:*)",
+      "Bash(.tox/*/bin/ruff:*)"
     ],
     "deny": []
   }
diff --git a/.github/workflows/ai-integration-test.yml b/.github/workflows/ai-integration-test.yml
index 63478440d4..65dd82967c 100644
--- a/.github/workflows/ai-integration-test.yml
+++ b/.github/workflows/ai-integration-test.yml
@@ -19,12 +19,12 @@ jobs:
 
     steps:
       - name: Setup Python
-        uses: actions/setup-python@v6
+        uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         with:
           python-version: 3.14t
 
       - name: Setup Node.js
-        uses: actions/setup-node@v6
+        uses: actions/setup-node@53b83947a5a98c8d113130e565377fae1a50d02f # v6
         with:
           node-version: '20'
 
@@ -34,7 +34,7 @@ jobs:
           token: ${{ secrets.GITHUB_TOKEN }}
 
       - name: Run Python SDK Tests
-        uses: getsentry/testing-ai-sdk-integrations@285c012e522f241581534dfc89bd99ec3b1da4f6
+        uses: getsentry/testing-ai-sdk-integrations@6b1f51ec8af03e19087df452b426aa7e46d2b20a
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
         with:
diff --git a/.github/workflows/changelog-preview.yml b/.github/workflows/changelog-preview.yml
index 3788b29609..2f683bdd75 100644
--- a/.github/workflows/changelog-preview.yml
+++ b/.github/workflows/changelog-preview.yml
@@ -15,5 +15,5 @@ permissions:
 
 jobs:
   changelog-preview:
-    uses: getsentry/craft/.github/workflows/changelog-preview.yml@v2
+    uses: getsentry/craft/.github/workflows/changelog-preview.yml@f4889d04564e47311038ecb6b910fef6b6cf1363 # v2
     secrets: inherit
diff --git a/.github/workflows/ci.yml b/.github/workflows/ci.yml
index 2c56d8375c..ee3d24db79 100644
--- a/.github/workflows/ci.yml
+++ b/.github/workflows/ci.yml
@@ -24,7 +24,7 @@ jobs:
 
     steps:
       - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         with:
           python-version: 3.14
 
@@ -39,11 +39,11 @@ jobs:
 
     steps:
       - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         with:
           python-version: 3.12
       - name: Setup build cache
-        uses: actions/cache@v5
+        uses: actions/cache@668228422ae6a00e4ad889ee87cd7109ec5666a7 # v5
         id: build_cache
         with:
           path: ${{ env.CACHED_BUILD_PATHS }}
@@ -54,7 +54,7 @@ jobs:
           # This will also trigger "make dist" that creates the Python packages
           make aws-lambda-layer
       - name: Upload Python Packages
-        uses: actions/upload-artifact@v7
+        uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7
         with:
           name: artifact-build_lambda_layer
           path: |
@@ -68,7 +68,7 @@ jobs:
 
     steps:
       - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         with:
           python-version: 3.12
 
@@ -76,7 +76,7 @@ jobs:
           make apidocs
           cd docs/_build && zip -r gh-pages ./
 
-      - uses: actions/upload-artifact@v7
+      - uses: actions/upload-artifact@bbbca2ddaa5d8feaa63e36b76fdaad77386f024f # v7
         with:
           name: artifact-docs
           path: |
diff --git a/.github/workflows/enforce-draft-pr.yml b/.github/workflows/enforce-draft-pr.yml
new file mode 100644
index 0000000000..6a5da12272
--- /dev/null
+++ b/.github/workflows/enforce-draft-pr.yml
@@ -0,0 +1,75 @@
+name: Enforce Draft PR
+
+on:
+  pull_request_target:
+    types: [opened, reopened]
+
+permissions:
+  pull-requests: write
+
+jobs:
+  enforce-draft:
+    name: Enforce Draft PR
+    runs-on: ubuntu-24.04
+    if: github.event.pull_request.draft == false
+    steps:
+      - name: Convert PR to draft
+        uses: actions/github-script@60a0d83039c74a4aee543508d2ffcb1c3799cdea  # v7.0.1
+        with:
+          script: |
+            const pullRequest = context.payload.pull_request;
+            const repo = context.repo;
+
+            // Convert to draft via GraphQL (REST API doesn't support this)
+            try {
+              await github.graphql(`
+                mutation($pullRequestId: ID!) {
+                  convertPullRequestToDraft(input: { pullRequestId: $pullRequestId }) {
+                    pullRequest {
+                      isDraft
+                    }
+                  }
+                }
+              `, {
+                pullRequestId: pullRequest.node_id
+              });
+            } catch (error) {
+              core.warning(`Failed to convert PR to draft: ${error.message}`);
+              return;
+            }
+
+            // Label the PR so maintainers can filter/track violations
+            await github.rest.issues.addLabels({
+              ...repo,
+              issue_number: pullRequest.number,
+              labels: ['converted-to-draft'],
+            });
+
+            // Check for existing bot comment to avoid duplicates on reopen
+            const comments = await github.rest.issues.listComments({
+              ...repo,
+              issue_number: pullRequest.number,
+            });
+            const botComment = comments.data.find(c =>
+              c.user.type === 'Bot' &&
+              c.body.includes('automatically converted to draft')
+            );
+            if (botComment) {
+              core.info('Bot comment already exists, skipping.');
+              return;
+            }
+
+            const contributingUrl = `https://github.com/${repo.owner}/${repo.repo}/blob/master/CONTRIBUTING.md`;
+
+            await github.rest.issues.createComment({
+              ...repo,
+              issue_number: pullRequest.number,
+              body: [
+                `This PR has been automatically converted to draft. All PRs must start as drafts per our [contributing guidelines](${contributingUrl}).`,
+                '',
+                '**Next steps:**',
+                '1. Ensure CI passes',
+                '2. Fill in the PR description completely',
+                '3. Mark as "Ready for review" when you\'re done'
+              ].join('\n')
+            });
diff --git a/.github/workflows/enforce-license-compliance.yml b/.github/workflows/enforce-license-compliance.yml
index 7cee2720e5..fece653550 100644
--- a/.github/workflows/enforce-license-compliance.yml
+++ b/.github/workflows/enforce-license-compliance.yml
@@ -18,6 +18,6 @@ jobs:
     runs-on: ubuntu-latest
     steps:
       - name: 'Enforce License Compliance'
-        uses: getsentry/action-enforce-license-compliance@main
+        uses: getsentry/action-enforce-license-compliance@48236a773346cb6552a7bda1ee370d2797365d87 # main
         with:
           fossa_api_key: ${{ secrets.FOSSA_API_KEY }}
diff --git a/.github/workflows/release-comment-issues.yml b/.github/workflows/release-comment-issues.yml
index e18aeab155..0203ff59ed 100644
--- a/.github/workflows/release-comment-issues.yml
+++ b/.github/workflows/release-comment-issues.yml
@@ -33,7 +33,7 @@ jobs:
           && !contains(steps.get_version.outputs.version, 'a')
           && !contains(steps.get_version.outputs.version, 'b')
           && !contains(steps.get_version.outputs.version, 'rc')
-        uses: getsentry/release-comment-issues-gh-action@v1
+        uses: getsentry/release-comment-issues-gh-action@52e08022ca721e701515ede89edd224b63b180eb # v1
         with:
           github_token: ${{ secrets.GITHUB_TOKEN }}
           version: ${{ steps.get_version.outputs.version }}
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
index 1d8fdb1000..b2a935fcea 100644
--- a/.github/workflows/release.yml
+++ b/.github/workflows/release.yml
@@ -22,7 +22,7 @@ jobs:
     steps:
     - name: Get auth token
       id: token
-      uses: actions/create-github-app-token@29824e69f54612133e76f7eaac726eef6c875baf # v2
+      uses: actions/create-github-app-token@f8d387b68d61c58ab83c6c016672934102569859 # v2
       with:
         app-id: ${{ vars.SENTRY_RELEASE_BOT_CLIENT_ID }}
         private-key: ${{ secrets.SENTRY_RELEASE_BOT_PRIVATE_KEY }}
@@ -31,7 +31,7 @@ jobs:
         token: ${{ steps.token.outputs.token }}
         fetch-depth: 0
     - name: Prepare release
-      uses: getsentry/craft@d4cfac9d25d1fc72c9241e5d22aff559a114e4e9 # v2
+      uses: getsentry/craft@013a7b2113c2cac0ff32d5180cfeaefc7c9ce5b6 # v2
       env:
         GITHUB_TOKEN: ${{ steps.token.outputs.token }}
       with:
diff --git a/.github/workflows/test-integrations-agents.yml b/.github/workflows/test-integrations-agents.yml
index a05649a5f0..fbb983ef03 100644
--- a/.github/workflows/test-integrations-agents.yml
+++ b/.github/workflows/test-integrations-agents.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -74,7 +74,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-ai-workflow.yml b/.github/workflows/test-integrations-ai-workflow.yml
index 7cd4cb86df..a3e2bf5c0e 100644
--- a/.github/workflows/test-integrations-ai-workflow.yml
+++ b/.github/workflows/test-integrations-ai-workflow.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -78,7 +78,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-ai.yml b/.github/workflows/test-integrations-ai.yml
index 0b305a3775..4a8d9a047d 100644
--- a/.github/workflows/test-integrations-ai.yml
+++ b/.github/workflows/test-integrations-ai.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -69,10 +69,6 @@ jobs:
         run: |
           set -x # print commands that are executed
           ./scripts/runtox.sh "py${{ matrix.python-version }}-huggingface_hub"
-      - name: Test litellm
-        run: |
-          set -x # print commands that are executed
-          ./scripts/runtox.sh "py${{ matrix.python-version }}-litellm"
       - name: Test openai-base
         run: |
           set -x # print commands that are executed
@@ -94,7 +90,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-cloud.yml b/.github/workflows/test-integrations-cloud.yml
index d57034d4e3..97aed9e30b 100644
--- a/.github/workflows/test-integrations-cloud.yml
+++ b/.github/workflows/test-integrations-cloud.yml
@@ -45,8 +45,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -90,7 +90,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-common.yml b/.github/workflows/test-integrations-common.yml
index 9b333435bd..6523ce084e 100644
--- a/.github/workflows/test-integrations-common.yml
+++ b/.github/workflows/test-integrations-common.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -70,7 +70,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-dbs.yml b/.github/workflows/test-integrations-dbs.yml
index c27d728b98..380ded2f80 100644
--- a/.github/workflows/test-integrations-dbs.yml
+++ b/.github/workflows/test-integrations-dbs.yml
@@ -59,14 +59,14 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
           allow-prereleases: true
       - name: "Setup ClickHouse Server"
-        uses: getsentry/action-clickhouse-in-ci@v1.7
+        uses: getsentry/action-clickhouse-in-ci@5dc8a6a50d689bd6051db0241f34849e5a36490b # v1.7
       - name: Setup Test Env
         run: |
           pip install "coverage[toml]" tox
@@ -110,7 +110,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-flags.yml b/.github/workflows/test-integrations-flags.yml
index cd20a6ec5e..13897537af 100644
--- a/.github/workflows/test-integrations-flags.yml
+++ b/.github/workflows/test-integrations-flags.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -82,7 +82,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-gevent.yml b/.github/workflows/test-integrations-gevent.yml
index 525140dfa7..934498b96c 100644
--- a/.github/workflows/test-integrations-gevent.yml
+++ b/.github/workflows/test-integrations-gevent.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -70,7 +70,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-graphql.yml b/.github/workflows/test-integrations-graphql.yml
index 322a95ff54..d26b4a422a 100644
--- a/.github/workflows/test-integrations-graphql.yml
+++ b/.github/workflows/test-integrations-graphql.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -82,7 +82,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-mcp.yml b/.github/workflows/test-integrations-mcp.yml
index 4b576a897f..0611f9a249 100644
--- a/.github/workflows/test-integrations-mcp.yml
+++ b/.github/workflows/test-integrations-mcp.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -74,7 +74,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-misc.yml b/.github/workflows/test-integrations-misc.yml
index 021d6cda79..8787acb8ca 100644
--- a/.github/workflows/test-integrations-misc.yml
+++ b/.github/workflows/test-integrations-misc.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -102,7 +102,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-network.yml b/.github/workflows/test-integrations-network.yml
index ee4579f50f..6bdb2e99ed 100644
--- a/.github/workflows/test-integrations-network.yml
+++ b/.github/workflows/test-integrations-network.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -78,7 +78,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-tasks.yml b/.github/workflows/test-integrations-tasks.yml
index bab5ddf335..085714d756 100644
--- a/.github/workflows/test-integrations-tasks.yml
+++ b/.github/workflows/test-integrations-tasks.yml
@@ -41,16 +41,16 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
           allow-prereleases: true
       - name: Start Redis
-        uses: supercharge/redis-github-action@v2
+        uses: supercharge/redis-github-action@87f27ff1ab2d9e62db54b11ee5e7f78ff18f8933 # v2
       - name: Install Java
-        uses: actions/setup-java@v5
+        uses: actions/setup-java@be666c2fcd27ec809703dec50e508c2fdc7f6654 # v5
         with:
           distribution: 'temurin'
           java-version: '21'
@@ -105,7 +105,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-web-1.yml b/.github/workflows/test-integrations-web-1.yml
index 82632632e7..48797f5dcf 100644
--- a/.github/workflows/test-integrations-web-1.yml
+++ b/.github/workflows/test-integrations-web-1.yml
@@ -59,8 +59,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -100,7 +100,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/test-integrations-web-2.yml b/.github/workflows/test-integrations-web-2.yml
index 9dec6bff24..87f69d36bd 100644
--- a/.github/workflows/test-integrations-web-2.yml
+++ b/.github/workflows/test-integrations-web-2.yml
@@ -41,8 +41,8 @@ jobs:
     # Use Docker container only for Python 3.6
     container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         if: ${{ matrix.python-version != '3.6' }}
         with:
           python-version: ${{ matrix.python-version }}
@@ -106,7 +106,7 @@ jobs:
           coverage xml
       - name: Parse and Upload Coverage
         if: ${{ !cancelled() }}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: ${{ secrets.GITHUB_TOKEN }}
           files: coverage.xml
diff --git a/.github/workflows/update-tox.yml b/.github/workflows/update-tox.yml
index 914109eae8..3c9bc456e1 100644
--- a/.github/workflows/update-tox.yml
+++ b/.github/workflows/update-tox.yml
@@ -18,7 +18,7 @@ jobs:
 
     steps:
       - name: Setup Python
-        uses: actions/setup-python@v6
+        uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         with:
           python-version: 3.14t
 
@@ -42,7 +42,7 @@ jobs:
         run: |
           COMMIT_TITLE="ci: 🤖 Update test matrix with new releases"
           DATE=`date +%m/%d`
-          BRANCH_NAME="toxgen/update"
+          BRANCH_NAME="toxgen/update-`date +%m-%d`"
 
           git checkout -B "$BRANCH_NAME"
           git add --all
@@ -54,7 +54,7 @@ jobs:
           echo "date=$DATE" >> $GITHUB_OUTPUT
 
       - name: Create pull request
-        uses: actions/github-script@v8
+        uses: actions/github-script@ed597411d8f924073f98dfc5c65a23a2325f34cd # v8
         with:
           script: |
             const branchName = '${{ steps.create-branch.outputs.branch_name }}';
@@ -78,20 +78,21 @@ jobs:
 
             // Close existing toxgen PRs as they're now obsolete
 
-            const { data: existingPRs } = await github.rest.pulls.list({
+            const existingPRs = await github.paginate(github.rest.pulls.list, {
                 owner: context.repo.owner,
                 repo: context.repo.repo,
-                head: `${context.repo.owner}:${branchName}`,
                 state: 'open'
             });
 
             for (const pr of existingPRs) {
-                await github.rest.pulls.update({
-                    owner: context.repo.owner,
-                    repo: context.repo.repo,
-                    pull_number: pr.number,
-                    state: 'closed'
-                })
+                if (pr.head.ref.startsWith('toxgen/')) {
+                    await github.rest.pulls.update({
+                        owner: context.repo.owner,
+                        repo: context.repo.repo,
+                        pull_number: pr.number,
+                        state: 'closed'
+                    })
+                }
             };
 
             const { data: pr } = await github.rest.pulls.create({
diff --git a/.github/workflows/warden.yml b/.github/workflows/warden.yml
deleted file mode 100644
index f2ff05325a..0000000000
--- a/.github/workflows/warden.yml
+++ /dev/null
@@ -1,24 +0,0 @@
-name: Warden
-
-on:
-  pull_request:
-    types: [opened, synchronize, reopened]
-
-# contents: write required for resolving review threads via GraphQL
-# See: https://github.com/orgs/community/discussions/44650
-permissions:
-  contents: write
-  pull-requests: write
-  checks: write
-
-jobs:
-  review:
-    runs-on: ubuntu-latest
-    env:
-      WARDEN_MODEL: ${{ secrets.WARDEN_MODEL }}
-      WARDEN_SENTRY_DSN: ${{ secrets.WARDEN_SENTRY_DSN }}
-    steps:
-      - uses: actions/checkout@v4
-      - uses: getsentry/warden@v0
-        with:
-          anthropic-api-key: ${{ secrets.WARDEN_ANTHROPIC_API_KEY }}
diff --git a/.gitignore b/.gitignore
index 4e35d43fb5..c5ae46befa 100644
--- a/.gitignore
+++ b/.gitignore
@@ -21,6 +21,8 @@ sentry-python-serverless*.zip
 .eggs
 venv
 .venv
+tox.venv
+toxgen.venv
 .vscode/tags
 .pytest_cache
 .hypothesis
diff --git a/AGENTS.md b/AGENTS.md
index 6179106348..f1b5c696df 100644
--- a/AGENTS.md
+++ b/AGENTS.md
@@ -11,6 +11,8 @@ Use **tox** for testing (not pytest directly):
 - Test matrix configuration is in `tox.ini`
 - Integration tests: `tox -e py3.14-{integration}-v{version}`
 - Common tests: `tox -e py3.14-common`
+- Run specific test file: `TESTPATH=tests/integrations/logging/test_logging.py tox -e py3.14-common`
+- Run single test: `TESTPATH=tests/path/to/test_file.py tox -e py3.14-common -- -k "test_name"`
 
 ## Type Checking
 
diff --git a/CHANGELOG.md b/CHANGELOG.md
index f21da70dda..99c4086129 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,5 +1,117 @@
 # Changelog
 
+## 2.56.0
+
+### New Features ✨
+
+- (asgi) Add option to disable suppressing chained exceptions by @alexander-alderman-webb in [#5714](https://github.com/getsentry/sentry-python/pull/5714)
+- (logging) Separate ignore lists for events/breadcrumbs and sentry logs by @sl0thentr0py in [#5698](https://github.com/getsentry/sentry-python/pull/5698)
+
+### Bug Fixes 🐛
+
+#### Anthropic
+
+- Set exception info on streaming span when applicable by @alexander-alderman-webb in [#5683](https://github.com/getsentry/sentry-python/pull/5683)
+- Patch `AsyncStream.close()` and `AsyncMessageStream.close()` to finish spans by @alexander-alderman-webb in [#5675](https://github.com/getsentry/sentry-python/pull/5675)
+- Patch `Stream.close()` and `MessageStream.close()` to finish spans by @alexander-alderman-webb in [#5674](https://github.com/getsentry/sentry-python/pull/5674)
+
+#### Other
+
+- (starlette) Catch Jinja2Templates ImportError by @alexander-alderman-webb in [#5741](https://github.com/getsentry/sentry-python/pull/5741)
+
+### Documentation 📚
+
+- Add note on AI PRs to CONTRIBUTING.md by @sentrivana in [#5696](https://github.com/getsentry/sentry-python/pull/5696)
+
+### Internal Changes 🔧
+
+- Pin GitHub Actions to full-length commit SHAs by @joshuarli in [#5781](https://github.com/getsentry/sentry-python/pull/5781)
+- Add `-latest` alias for each integration test suite by @sentrivana in [#5706](https://github.com/getsentry/sentry-python/pull/5706)
+- Use date-based branch names for toxgen PRs by @sentrivana in [#5704](https://github.com/getsentry/sentry-python/pull/5704)
+- 🤖 Update test matrix with new releases (03/19) by @github-actions in [#5703](https://github.com/getsentry/sentry-python/pull/5703)
+- Add client report tests for span streaming by @sentrivana in [#5677](https://github.com/getsentry/sentry-python/pull/5677)
+
+### Other
+
+- Update CHANGELOG.md by @sentrivana in [#5685](https://github.com/getsentry/sentry-python/pull/5685)
+
+## 2.55.0
+
+### New Features ✨
+
+#### Anthropic
+
+- Record finish reasons in AI monitoring spans by @ericapisani in [#5678](https://github.com/getsentry/sentry-python/pull/5678)
+- Emit `gen_ai.chat` spans for asynchronous `messages.stream()` by @alexander-alderman-webb in [#5572](https://github.com/getsentry/sentry-python/pull/5572)
+- Emit AI Client Spans for synchronous `messages.stream()` by @alexander-alderman-webb in [#5565](https://github.com/getsentry/sentry-python/pull/5565)
+- Set gen_ai.response.id span attribute by @ericapisani in [#5662](https://github.com/getsentry/sentry-python/pull/5662)
+- Add `gen_ai.system` attribute to spans by @ericapisani in [#5661](https://github.com/getsentry/sentry-python/pull/5661)
+
+#### Pydantic Ai
+
+- Support ImageUrl content type in span instrumentation by @ericapisani in [#5629](https://github.com/getsentry/sentry-python/pull/5629)
+- Add tool description to execute_tool spans by @ericapisani in [#5596](https://github.com/getsentry/sentry-python/pull/5596)
+
+#### Other
+
+- (crons) Add owner field to MonitorConfig by @julwhitney13 in [#5610](https://github.com/getsentry/sentry-python/pull/5610)
+- (otlp) Add collector_url option to OTLPIntegration by @sl0thentr0py in [#5603](https://github.com/getsentry/sentry-python/pull/5603)
+
+### Bug Fixes 🐛
+
+- (ai) Truncate list-based message content in AI monitoring by @ericapisani in [#5631](https://github.com/getsentry/sentry-python/pull/5631)
+- (anthropic) Close span on `GeneratorExit` by @alexander-alderman-webb in [#5643](https://github.com/getsentry/sentry-python/pull/5643)
+- (celery) Propagate user-set headers by @sentrivana in [#5581](https://github.com/getsentry/sentry-python/pull/5581)
+- (langchain) Wrap finish_reason in array for gen_ai span attribute by @ericapisani in [#5666](https://github.com/getsentry/sentry-python/pull/5666)
+- (logging) Fix deadlock in log batcher by @sentrivana in [#5684](https://github.com/getsentry/sentry-python/pull/5684)
+- (profiler) Prevent buffer race condition during rapid start/stop cycles by @ericapisani in [#5622](https://github.com/getsentry/sentry-python/pull/5622)
+- (utils) Avoid double serialization of strings in safe_serialize by @ericapisani in [#5587](https://github.com/getsentry/sentry-python/pull/5587)
+- Enable unused import ruff check and fix unused imports by @sentrivana in [#5652](https://github.com/getsentry/sentry-python/pull/5652)
+
+### Documentation 📚
+
+- (openai-agents) Remove inapplicable comment by @alexander-alderman-webb in [#5495](https://github.com/getsentry/sentry-python/pull/5495)
+- Add AGENTS.md by @sentrivana in [#5579](https://github.com/getsentry/sentry-python/pull/5579)
+- Add `set_attribute` example to changelog by @sentrivana in [#5578](https://github.com/getsentry/sentry-python/pull/5578)
+
+### Internal Changes 🔧
+
+#### Anthropic
+
+- Check system and response ID attributes on spans created by `stream()` by @alexander-alderman-webb in [#5665](https://github.com/getsentry/sentry-python/pull/5665)
+- Skip accumulation logic for unexpected types in streamed response by @alexander-alderman-webb in [#5564](https://github.com/getsentry/sentry-python/pull/5564)
+- Factor out streamed result handling by @alexander-alderman-webb in [#5563](https://github.com/getsentry/sentry-python/pull/5563)
+- Stream valid JSON by @alexander-alderman-webb in [#5641](https://github.com/getsentry/sentry-python/pull/5641)
+- Stop mocking response iterator by @alexander-alderman-webb in [#5573](https://github.com/getsentry/sentry-python/pull/5573)
+
+#### Openai Agents
+
+- Do not fail on new tool fields by @alexander-alderman-webb in [#5625](https://github.com/getsentry/sentry-python/pull/5625)
+- Stop expecting a specific function name by @alexander-alderman-webb in [#5623](https://github.com/getsentry/sentry-python/pull/5623)
+- Set streaming header when library uses `with_streaming_response()` by @alexander-alderman-webb in [#5583](https://github.com/getsentry/sentry-python/pull/5583)
+- Replace mocks with `httpx` for streamed responses by @alexander-alderman-webb in [#5580](https://github.com/getsentry/sentry-python/pull/5580)
+- Replace mocks with `httpx` in non-MCP tool tests by @alexander-alderman-webb in [#5602](https://github.com/getsentry/sentry-python/pull/5602)
+- Replace mocks with `httpx` in MCP tool tests by @alexander-alderman-webb in [#5605](https://github.com/getsentry/sentry-python/pull/5605)
+- Replace mocks with `httpx` in handoff tests by @alexander-alderman-webb in [#5604](https://github.com/getsentry/sentry-python/pull/5604)
+- Replace mocks with `httpx` in API error test by @alexander-alderman-webb in [#5601](https://github.com/getsentry/sentry-python/pull/5601)
+- Replace mocks with `httpx` in non-error single-response tests by @alexander-alderman-webb in [#5600](https://github.com/getsentry/sentry-python/pull/5600)
+- Remove test for unreachable state by @alexander-alderman-webb in [#5584](https://github.com/getsentry/sentry-python/pull/5584)
+- Expect `namespace` tool field for new `openai` versions by @alexander-alderman-webb in [#5599](https://github.com/getsentry/sentry-python/pull/5599)
+
+#### Other
+
+- (graphene) Simplify span creation by @sentrivana in [#5648](https://github.com/getsentry/sentry-python/pull/5648)
+- (httpx) Resolve type checking failures by @alexander-alderman-webb in [#5626](https://github.com/getsentry/sentry-python/pull/5626)
+- (pyramid) Support alpha suffixes in version parsing by @alexander-alderman-webb in [#5618](https://github.com/getsentry/sentry-python/pull/5618)
+- (rust) Don't implement separate scope management by @sentrivana in [#5639](https://github.com/getsentry/sentry-python/pull/5639)
+- (strawberry) Simplify span creation by @sentrivana in [#5647](https://github.com/getsentry/sentry-python/pull/5647)
+- 🤖 Update test matrix with new releases (03/16) by @github-actions in [#5671](https://github.com/getsentry/sentry-python/pull/5671)
+- Remove custom warden action by @sentrivana in [#5653](https://github.com/getsentry/sentry-python/pull/5653)
+- Add `httpx` to linting requirements by @alexander-alderman-webb in [#5644](https://github.com/getsentry/sentry-python/pull/5644)
+- Remove CodeQL action by @sentrivana in [#5616](https://github.com/getsentry/sentry-python/pull/5616)
+- Normalize dots in package names in `populate_tox.py` by @alexander-alderman-webb in [#5574](https://github.com/getsentry/sentry-python/pull/5574)
+- Do not run actions on `potel-base` by @sentrivana in [#5614](https://github.com/getsentry/sentry-python/pull/5614)
+
 ## 2.54.0
 
 ### New Features ✨
diff --git a/CONTRIBUTING.md b/CONTRIBUTING.md
index 0286a3170e..e0c7b1cc9e 100644
--- a/CONTRIBUTING.md
+++ b/CONTRIBUTING.md
@@ -10,6 +10,10 @@ Please search the [issue tracker](https://github.com/getsentry/sentry-python/iss
 
 ## Submitting Changes
 
+Before submitting a pull request, please check whether the issue you're planning to address, if there is one, is assigned to anyone. If you want to help with an issue that already has an assignee, comment on it first to coordinate with the person assigned whether the contribution would make sense before opening a pull request.
+
+To make a contribution:
+
 - Fork the `sentry-python` repo and prepare your changes.
 - Add tests for your changes to `tests/`.
 - Run tests and make sure all of them pass.
@@ -17,6 +21,22 @@ Please search the [issue tracker](https://github.com/getsentry/sentry-python/iss
 
 We will review your pull request as soon as possible. Thank you for contributing!
 
+### AI Use
+
+You are welcome to use whatever tools you prefer for making a contribution. However, any changes you propose have to be reviewed and tested by you, a human, first, before you submit a pull request with them for the Sentry team to review. If we feel like that didn't happen, we will close the PR outright. For example, we won't review visibly AI-generated PRs from an agent instructed to look for and "fix" open issues in the repo.
+
+## Pull Requests
+
+All PRs must be created as **drafts**. Non-draft PRs will be automatically converted to draft. Mark your PR as "Ready for review" once:
+
+- CI passes
+- The PR description is complete (what, why, and links to relevant issues)
+- You've personally reviewed your own changes
+
+A PR should do one thing well. Don't mix functional changes with unrelated refactors or cleanup. Smaller, focused PRs are easier to review, reason about, and revert if needed.
+
+For the full set of PR standards, see the [code submission standard](https://develop.sentry.dev/sdk/getting-started/standards/code-submission/#pull-requests).
+
 ## Development Environment
 
 ### Set up Python
diff --git a/docs/conf.py b/docs/conf.py
index a3ecc64b9b..c2af338111 100644
--- a/docs/conf.py
+++ b/docs/conf.py
@@ -31,7 +31,7 @@
 copyright = "2019-{}, Sentry Team and Contributors".format(datetime.now().year)
 author = "Sentry Team and Contributors"
 
-release = "2.54.0"
+release = "2.56.0"
 version = ".".join(release.split(".")[:2])  # The short X.Y version.
 
 
diff --git a/pyproject.toml b/pyproject.toml
index 4b3d72ea09..b090d9bd4d 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -227,7 +227,6 @@ ignore = [
     "N804", # First argument of classmethod should be named cls
 
     # Additional ignores for codebase compatibility
-    "F401", # Unused imports - many in TYPE_CHECKING blocks used for type comments
     "E721", # Use isinstance instead of type() == - existing pattern in this codebase
 ]
 
diff --git a/requirements-testing.txt b/requirements-testing.txt
index 5cd669af9a..a6041972cd 100644
--- a/requirements-testing.txt
+++ b/requirements-testing.txt
@@ -4,6 +4,7 @@ tomli;python_version<"3.11"  # Only needed for pytest on Python < 3.11
 pytest-cov
 pytest-forked
 pytest-localserver
+pytest-timeout
 pytest-watch
 jsonschema
 executing
diff --git a/scripts/populate_tox/config.py b/scripts/populate_tox/config.py
index c6921754b4..2fdb04ba8e 100644
--- a/scripts/populate_tox/config.py
+++ b/scripts/populate_tox/config.py
@@ -123,6 +123,7 @@
                 "python-multipart",
                 "requests",
                 "anyio<4",
+                "jinja2",
             ],
             # There's an incompatibility between FastAPI's TestClient, which is
             # actually Starlette's TestClient, which is actually httpx's Client.
@@ -229,9 +230,6 @@
         "package": "launchdarkly-server-sdk",
         "num_versions": 2,
     },
-    "litellm": {
-        "package": "litellm",
-    },
     "litestar": {
         "package": "litestar",
         "deps": {
diff --git a/scripts/populate_tox/package_dependencies.jsonl b/scripts/populate_tox/package_dependencies.jsonl
index b46a00ab90..aad403ba6e 100644
--- a/scripts/populate_tox/package_dependencies.jsonl
+++ b/scripts/populate_tox/package_dependencies.jsonl
@@ -1,6 +1,6 @@
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diff --git a/scripts/populate_tox/populate_tox.py b/scripts/populate_tox/populate_tox.py
index 7f1065378e..fa0c31a3d1 100644
--- a/scripts/populate_tox/populate_tox.py
+++ b/scripts/populate_tox/populate_tox.py
@@ -20,7 +20,6 @@
 from packaging.specifiers import SpecifierSet
 from packaging.version import Version
 from pathlib import Path
-from textwrap import dedent
 from typing import Optional, Union
 
 # Adding the scripts directory to PATH. This is necessary in order to be able
@@ -725,6 +724,31 @@ def _render_dependencies(integration: str, releases: list[Version]) -> list[str]
     return rendered
 
 
+def _render_latest_dependencies(
+    integration: str, latest_release: Version
+) -> list[str]:
+    """Render version-specific dependencies for the 'latest' alias.
+
+    Dependencies with "*" or "py3.*" constraints already match the latest
+    env via tox factor matching, so only version-specific constraints need
+    to be duplicated here.
+    """
+    rendered = []
+
+    if TEST_SUITE_CONFIG[integration].get("deps") is None:
+        return rendered
+
+    for constraint, deps in TEST_SUITE_CONFIG[integration]["deps"].items():
+        if constraint == "*" or constraint.startswith("py3"):
+            continue
+        restriction = SpecifierSet(constraint, prereleases=True)
+        if latest_release in restriction:
+            for dep in deps:
+                rendered.append(f"{integration}-latest: {dep}")
+
+    return rendered
+
+
 def write_tox_file(packages: dict) -> None:
     template = ENV.get_template("tox.jinja")
 
@@ -736,15 +760,30 @@ def write_tox_file(packages: dict) -> None:
     for group, integrations in packages.items():
         context["groups"][group] = []
         for integration in integrations:
+            # Find the highest stable (non-prerelease) release for the
+            # -latest alias.  Prereleases are always appended last by
+            # pick_releases_to_test, so we walk backwards.
+            latest_stable = None
+            for rel in reversed(integration["releases"]):
+                if not rel.is_prerelease:
+                    latest_stable = rel
+                    break
+
             context["groups"][group].append(
                 {
                     "name": integration["name"],
                     "package": integration["package"],
                     "extra": integration["extra"],
                     "releases": integration["releases"],
+                    "latest_stable": latest_stable,
                     "dependencies": _render_dependencies(
                         integration["name"], integration["releases"]
                     ),
+                    "latest_dependencies": _render_latest_dependencies(
+                        integration["name"], latest_stable
+                    )
+                    if latest_stable
+                    else [],
                 }
             )
             context["testpaths"].append(
diff --git a/scripts/populate_tox/releases.jsonl b/scripts/populate_tox/releases.jsonl
index 835d769ec1..6015492fda 100644
--- a/scripts/populate_tox/releases.jsonl
+++ b/scripts/populate_tox/releases.jsonl
@@ -18,7 +18,7 @@
 {"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Intended Audience :: Developers", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.7", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: 3.9", "Programming Language :: Python :: Implementation :: CPython", "Programming Language :: Python :: Implementation :: PyPy", "Topic :: Database :: Front-Ends"], "name": "SQLAlchemy", "requires_python": ">=3.7", "version": "2.0.48", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "sqlalchemy-2.0.48-cp310-cp310-macosx_11_0_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": 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-{"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Console", "Environment :: No Input/Output (Daemon)", "Framework :: Tryton", "Intended Audience :: Developers", "License :: OSI Approved :: GNU General Public License v3 or later (GPLv3+)", "Natural Language :: Bulgarian", "Natural Language :: Catalan", "Natural Language :: Chinese (Simplified)", "Natural Language :: Czech", "Natural Language :: Dutch", "Natural Language :: English", "Natural Language :: Finnish", "Natural Language :: French", "Natural Language :: German", "Natural Language :: Hungarian", "Natural Language :: Indonesian", "Natural Language :: Italian", "Natural Language :: Persian", "Natural Language :: Polish", "Natural Language :: Portuguese (Brazilian)", "Natural Language :: Romanian", "Natural Language :: Russian", "Natural Language :: Slovenian", "Natural Language :: Spanish", "Natural Language :: Turkish", "Natural Language :: Ukrainian", "Operating System :: OS Independent", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.9", "Programming Language :: Python :: Implementation :: CPython", "Topic :: Software Development :: Libraries :: Application Frameworks"], "name": "trytond", "requires_python": ">=3.9", "version": "7.8.5", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "trytond-7.8.5-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "trytond-7.8.5.tar.gz"}]}
+{"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Environment :: Console", "Environment :: No Input/Output (Daemon)", "Framework :: Tryton", "Intended Audience :: Developers", "License :: OSI Approved :: GNU General Public License v3 or later (GPLv3+)", "Natural Language :: Bulgarian", "Natural Language :: Catalan", "Natural Language :: Chinese (Simplified)", "Natural Language :: Czech", "Natural Language :: Dutch", "Natural Language :: English", "Natural Language :: Finnish", "Natural Language :: French", "Natural Language :: German", "Natural Language :: Hungarian", "Natural Language :: Indonesian", "Natural Language :: Italian", "Natural Language :: Persian", "Natural Language :: Polish", "Natural Language :: Portuguese (Brazilian)", "Natural Language :: Romanian", "Natural Language :: Russian", "Natural Language :: Slovenian", "Natural Language :: Spanish", "Natural Language :: Turkish", "Natural Language :: Ukrainian", "Operating System :: OS Independent", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.9", "Programming Language :: Python :: Implementation :: CPython", "Topic :: Software Development :: Libraries :: Application Frameworks"], "name": "trytond", "requires_python": ">=3.9", "version": "7.8.6", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "trytond-7.8.6-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "trytond-7.8.6.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 4 - Beta", "Intended Audience :: Developers", "Intended Audience :: Information Technology", "Intended Audience :: System Administrators", "License :: OSI Approved :: MIT License", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.7", "Programming Language :: Python :: 3.8", "Programming Language :: Python :: 3.9", "Topic :: Software Development", "Topic :: Software Development :: Libraries", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules", "Typing :: Typed"], "name": "typer", "requires_python": ">=3.7", "version": "0.15.4", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "typer-0.15.4-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "typer-0.15.4.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 4 - Beta", "Intended Audience :: Developers", "Intended Audience :: Information Technology", "Intended Audience :: System Administrators", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Topic :: Software Development", "Topic :: Software Development :: Libraries", "Topic :: Software Development :: Libraries :: Application Frameworks", "Topic :: Software Development :: Libraries :: Python Modules", "Typing :: Typed"], "name": "typer", "requires_python": ">=3.10", "version": "0.24.1", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "typer-0.24.1-py3-none-any.whl"}, {"packagetype": "sdist", "filename": "typer-0.24.1.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 4 - Beta", "Intended Audience :: Developers", "License :: OSI Approved :: BSD License", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Programming Language :: Python :: 3.9", "Programming Language :: Rust"], "name": "uuid_utils", "requires_python": ">=3.9", "version": "0.14.0", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-macosx_10_12_x86_64.macosx_11_0_arm64.macosx_10_12_universal2.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-macosx_10_12_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_17_armv7l.manylinux2014_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-manylinux_2_5_i686.manylinux1_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-musllinux_1_2_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-musllinux_1_2_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-musllinux_1_2_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-musllinux_1_2_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-win32.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-cp39-abi3-win_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-macosx_10_12_x86_64.macosx_11_0_arm64.macosx_10_12_universal2.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-macosx_10_12_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_17_aarch64.manylinux2014_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_17_armv7l.manylinux2014_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.0-pp311-pypy311_pp73-manylinux_2_5_i686.manylinux1_i686.whl"}, {"packagetype": "sdist", "filename": "uuid_utils-0.14.0.tar.gz"}]}
+{"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Intended Audience :: Developers", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Programming Language :: Python :: 3.9", "Programming Language :: Rust"], "name": "uuid_utils", "requires_python": ">=3.9", "version": "0.14.1", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-macosx_10_12_x86_64.macosx_11_0_arm64.macosx_10_12_universal2.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-macosx_10_12_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-manylinux_2_17_aarch64.manylinux2014_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-manylinux_2_17_armv7l.manylinux2014_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-manylinux_2_5_i686.manylinux1_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-musllinux_1_2_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-musllinux_1_2_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-musllinux_1_2_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-musllinux_1_2_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-win32.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-cp39-abi3-win_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-pp311-pypy311_pp73-macosx_10_12_x86_64.macosx_11_0_arm64.macosx_10_12_universal2.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-pp311-pypy311_pp73-macosx_10_12_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-pp311-pypy311_pp73-manylinux_2_17_aarch64.manylinux2014_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-pp311-pypy311_pp73-manylinux_2_17_armv7l.manylinux2014_armv7l.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-pp311-pypy311_pp73-manylinux_2_17_ppc64le.manylinux2014_ppc64le.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-pp311-pypy311_pp73-manylinux_2_17_x86_64.manylinux2014_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "uuid_utils-0.14.1-pp311-pypy311_pp73-manylinux_2_5_i686.manylinux1_i686.whl"}, {"packagetype": "sdist", "filename": "uuid_utils-0.14.1.tar.gz"}]}
 {"info": {"classifiers": ["Development Status :: 5 - Production/Stable", "Intended Audience :: Developers", "Operating System :: OS Independent", "Programming Language :: Python", "Programming Language :: Python :: 3", "Programming Language :: Python :: 3 :: Only", "Programming Language :: Python :: 3.10", "Programming Language :: Python :: 3.11", "Programming Language :: Python :: 3.12", "Programming Language :: Python :: 3.13", "Programming Language :: Python :: 3.14", "Programming Language :: Python :: Implementation :: CPython", "Programming Language :: Python :: Implementation :: PyPy"], "name": "zope.interface", "requires_python": ">=3.10", "version": "8.2", "yanked": false}, "urls": [{"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp310-cp310-macosx_10_9_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp310-cp310-macosx_11_0_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp310-cp310-manylinux1_i686.manylinux2014_i686.manylinux_2_17_i686.manylinux_2_5_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp310-cp310-manylinux1_x86_64.manylinux2014_x86_64.manylinux_2_17_x86_64.manylinux_2_5_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp310-cp310-manylinux2014_aarch64.manylinux_2_17_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp310-cp310-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp311-cp311-macosx_10_9_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp311-cp311-macosx_11_0_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp311-cp311-manylinux1_i686.manylinux2014_i686.manylinux_2_17_i686.manylinux_2_5_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp311-cp311-manylinux1_x86_64.manylinux2014_x86_64.manylinux_2_17_x86_64.manylinux_2_5_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp311-cp311-manylinux2014_aarch64.manylinux_2_17_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp311-cp311-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp312-cp312-macosx_10_9_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp312-cp312-macosx_11_0_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp312-cp312-manylinux1_i686.manylinux2014_i686.manylinux_2_17_i686.manylinux_2_5_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp312-cp312-manylinux1_x86_64.manylinux2014_x86_64.manylinux_2_17_x86_64.manylinux_2_5_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp312-cp312-manylinux2014_aarch64.manylinux_2_17_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp312-cp312-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp313-cp313-macosx_10_9_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp313-cp313-macosx_11_0_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp313-cp313-manylinux1_i686.manylinux2014_i686.manylinux_2_17_i686.manylinux_2_5_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp313-cp313-manylinux1_x86_64.manylinux2014_x86_64.manylinux_2_17_x86_64.manylinux_2_5_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp313-cp313-manylinux2014_aarch64.manylinux_2_17_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp313-cp313-win_amd64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp314-cp314-macosx_10_9_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp314-cp314-macosx_11_0_arm64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp314-cp314-manylinux1_i686.manylinux2014_i686.manylinux_2_17_i686.manylinux_2_5_i686.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp314-cp314-manylinux1_x86_64.manylinux2014_x86_64.manylinux_2_17_x86_64.manylinux_2_5_x86_64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp314-cp314-manylinux2014_aarch64.manylinux_2_17_aarch64.whl"}, {"packagetype": "bdist_wheel", "filename": "zope_interface-8.2-cp314-cp314-win_amd64.whl"}, {"packagetype": "sdist", "filename": "zope_interface-8.2.tar.gz"}]}
diff --git a/scripts/populate_tox/tox.jinja b/scripts/populate_tox/tox.jinja
index 1808a7c521..6a6d1a54c9 100755
--- a/scripts/populate_tox/tox.jinja
+++ b/scripts/populate_tox/tox.jinja
@@ -61,6 +61,9 @@ envlist =
     {% for release in integration.releases %}
     {{ release.rendered_python_versions }}-{{ integration.name }}-v{{ release }}
     {% endfor %}
+    {% if integration.latest_stable %}
+    {{ integration.latest_stable.rendered_python_versions }}-{{ integration.name }}-latest
+    {% endif %}
 
     {% endfor %}
 
@@ -143,9 +146,19 @@ deps =
     {{ integration.name }}-v{{ release }}: {{ integration.package }}=={{ release }}
     {% endif %}
     {% endfor %}
+    {% if integration.latest_stable %}
+    {% if integration.extra %}
+    {{ integration.name }}-latest: {{ integration.package }}[{{ integration.extra }}]=={{ integration.latest_stable }}
+    {% else %}
+    {{ integration.name }}-latest: {{ integration.package }}=={{ integration.latest_stable }}
+    {% endif %}
+    {% endif %}
     {% for dep in integration.dependencies %}
     {{ dep }}
     {% endfor %}
+    {% for dep in integration.latest_dependencies %}
+    {{ dep }}
+    {% endfor %}
 
     {% endfor %}
 
@@ -168,22 +181,22 @@ setenv =
     gevent: PYTEST_ADDOPTS="--ignore=tests/test_shadowed_module.py"
 
     # TESTPATH definitions for test suites not managed by toxgen
-    common: TESTPATH=tests
-    gevent: TESTPATH=tests
-    integration_deactivation: TESTPATH=tests/test_ai_integration_deactivation.py
-    shadowed_module: TESTPATH=tests/test_shadowed_module.py
-    asgi: TESTPATH=tests/integrations/asgi
-    aws_lambda: TESTPATH=tests/integrations/aws_lambda
-    cloud_resource_context: TESTPATH=tests/integrations/cloud_resource_context
-    gcp: TESTPATH=tests/integrations/gcp
-    opentelemetry: TESTPATH=tests/integrations/opentelemetry
-    otlp: TESTPATH=tests/integrations/otlp
-    potel: TESTPATH=tests/integrations/opentelemetry
-    socket: TESTPATH=tests/integrations/socket
+    common: _TESTPATH=tests
+    gevent: _TESTPATH=tests
+    integration_deactivation: _TESTPATH=tests/test_ai_integration_deactivation.py
+    shadowed_module: _TESTPATH=tests/test_shadowed_module.py
+    asgi: _TESTPATH=tests/integrations/asgi
+    aws_lambda: _TESTPATH=tests/integrations/aws_lambda
+    cloud_resource_context: _TESTPATH=tests/integrations/cloud_resource_context
+    gcp: _TESTPATH=tests/integrations/gcp
+    opentelemetry: _TESTPATH=tests/integrations/opentelemetry
+    otlp: _TESTPATH=tests/integrations/otlp
+    potel: _TESTPATH=tests/integrations/opentelemetry
+    socket: _TESTPATH=tests/integrations/socket
 
     # These TESTPATH definitions are auto-generated by toxgen
     {% for integration, testpath in testpaths %}
-    {{ integration }}: TESTPATH={{ testpath }}
+    {{ integration }}: _TESTPATH={{ testpath }}
     {% endfor %}
 
 passenv =
@@ -191,6 +204,7 @@ passenv =
     SENTRY_PYTHON_TEST_POSTGRES_USER
     SENTRY_PYTHON_TEST_POSTGRES_PASSWORD
     SENTRY_PYTHON_TEST_POSTGRES_NAME
+    TESTPATH
 
 usedevelop = True
 
@@ -228,7 +242,7 @@ commands =
     ; Running `pytest` as an executable suffers from an import error
     ; when loading tests in scenarios. In particular, django fails to
     ; load the settings from the test module.
-    python -m pytest -W error::pytest.PytestUnraisableExceptionWarning {env:TESTPATH} -o junit_suite_name={envname} {posargs}
+    python -m pytest -W error::pytest.PytestUnraisableExceptionWarning {env:TESTPATH:{env:_TESTPATH}} -o junit_suite_name={envname} {posargs}
 
 [testenv:linters]
 commands =
diff --git a/scripts/runtox.sh b/scripts/runtox.sh
index bd6e954947..77aab28ae3 100755
--- a/scripts/runtox.sh
+++ b/scripts/runtox.sh
@@ -15,7 +15,12 @@ fi
 
 searchstring="$1"
 
-ENV="$($TOXPATH -l | grep -- "$searchstring" | tr $'\n' ',')"
+# Filter out -latest environments unless explicitly requested
+if [[ "$searchstring" == *-latest* ]]; then
+    ENV="$($TOXPATH -l | grep -- "$searchstring" | tr $'\n' ',')"
+else
+    ENV="$($TOXPATH -l | grep -- "$searchstring" | grep -v -- '-latest$' | tr $'\n' ',')"
+fi
 
 if [ -z "${ENV}" ]; then
     echo "No targets found. Skipping."
diff --git a/scripts/split_tox_gh_actions/split_tox_gh_actions.py b/scripts/split_tox_gh_actions/split_tox_gh_actions.py
index b59e768a56..962c095351 100755
--- a/scripts/split_tox_gh_actions/split_tox_gh_actions.py
+++ b/scripts/split_tox_gh_actions/split_tox_gh_actions.py
@@ -87,7 +87,6 @@
         "cohere",
         "google_genai",
         "huggingface_hub",
-        "litellm",
         "openai-base",
         "openai-notiktoken",
     ],
@@ -240,6 +239,11 @@ def parse_tox():
             raw_python_versions = groups["py_versions"]
             framework = groups["framework"]
 
+            # The -latest env is an alias for the highest version of the
+            # same framework, so merge it with the base framework.
+            if framework.endswith("-latest"):
+                framework = framework[: -len("-latest")]
+
             # collect python versions to test the framework in
             raw_python_versions = set(raw_python_versions.split(","))
             py_versions[framework] |= raw_python_versions
diff --git a/scripts/split_tox_gh_actions/templates/test_group.jinja b/scripts/split_tox_gh_actions/templates/test_group.jinja
index bec1a0f835..fa6d31c55f 100644
--- a/scripts/split_tox_gh_actions/templates/test_group.jinja
+++ b/scripts/split_tox_gh_actions/templates/test_group.jinja
@@ -42,8 +42,8 @@
     # Use Docker container only for Python 3.6
     {% raw %}container: ${{ matrix.python-version == '3.6' && 'python:3.6' || null }}{% endraw %}
     steps:
-      - uses: actions/checkout@v6.0.2
-      - uses: actions/setup-python@v6
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+      - uses: actions/setup-python@a309ff8b426b58ec0e2a45f0f869d46889d02405 # v6
         {% raw %}if: ${{ matrix.python-version != '3.6' }}{% endraw %}
         with:
           python-version: {% raw %}${{ matrix.python-version }}{% endraw %}
@@ -51,17 +51,17 @@
 
       {% if needs_clickhouse %}
       - name: "Setup ClickHouse Server"
-        uses: getsentry/action-clickhouse-in-ci@v1.7
+        uses: getsentry/action-clickhouse-in-ci@5dc8a6a50d689bd6051db0241f34849e5a36490b # v1.7
       {% endif %}
 
       {% if needs_redis %}
       - name: Start Redis
-        uses: supercharge/redis-github-action@v2
+        uses: supercharge/redis-github-action@87f27ff1ab2d9e62db54b11ee5e7f78ff18f8933 # v2
       {% endif %}
 
       {% if needs_java %}
       - name: Install Java
-        uses: actions/setup-java@v5
+        uses: actions/setup-java@be666c2fcd27ec809703dec50e508c2fdc7f6654 # v5
         with:
           distribution: 'temurin'
           java-version: '21'
@@ -96,7 +96,7 @@
 
       - name: Parse and Upload Coverage
         if: {% raw %}${{ !cancelled() }}{% endraw %}
-        uses: getsentry/codecov-action@main
+        uses: getsentry/codecov-action@fda17cfc37e16a0cc23f61685813390bfee7daf3 # main
         with:
           token: {% raw %}${{ secrets.GITHUB_TOKEN }}{% endraw %}
           files: coverage.xml
diff --git a/sentry_sdk/_batcher.py b/sentry_sdk/_batcher.py
index 4a6ee07e67..4ba8046814 100644
--- a/sentry_sdk/_batcher.py
+++ b/sentry_sdk/_batcher.py
@@ -4,7 +4,7 @@
 from datetime import datetime, timezone
 from typing import TYPE_CHECKING, TypeVar, Generic
 
-from sentry_sdk.utils import format_timestamp, safe_repr, serialize_attribute
+from sentry_sdk.utils import format_timestamp
 from sentry_sdk.envelope import Envelope, Item, PayloadRef
 
 if TYPE_CHECKING:
@@ -31,6 +31,7 @@ def __init__(
         self._record_lost_func = record_lost_func
         self._running = True
         self._lock = threading.Lock()
+        self._active: "threading.local" = threading.local()
 
         self._flush_event: "threading.Event" = threading.Event()
 
@@ -70,23 +71,40 @@ def _ensure_thread(self) -> bool:
         return True
 
     def _flush_loop(self) -> None:
+        # Mark the flush-loop thread as active for its entire lifetime so
+        # that any re-entrant add() triggered by GC warnings during wait(),
+        # flush(), or Event operations is silently dropped instead of
+        # deadlocking on internal locks.
+        self._active.flag = True
         while self._running:
             self._flush_event.wait(self.FLUSH_WAIT_TIME + random.random())
             self._flush_event.clear()
             self._flush()
 
     def add(self, item: "T") -> None:
-        if not self._ensure_thread() or self._flusher is None:
+        # Bail out if the current thread is already executing batcher code.
+        # This prevents deadlocks when code running inside the batcher (e.g.
+        # _add_to_envelope during flush, or _flush_event.wait/set) triggers
+        # a GC-emitted warning that routes back through the logging
+        # integration into add().
+        if getattr(self._active, "flag", False):
             return None
 
-        with self._lock:
-            if len(self._buffer) >= self.MAX_BEFORE_DROP:
-                self._record_lost(item)
+        self._active.flag = True
+        try:
+            if not self._ensure_thread() or self._flusher is None:
                 return None
 
-            self._buffer.append(item)
-            if len(self._buffer) >= self.MAX_BEFORE_FLUSH:
-                self._flush_event.set()
+            with self._lock:
+                if len(self._buffer) >= self.MAX_BEFORE_DROP:
+                    self._record_lost(item)
+                    return None
+
+                self._buffer.append(item)
+                if len(self._buffer) >= self.MAX_BEFORE_FLUSH:
+                    self._flush_event.set()
+        finally:
+            self._active.flag = False
 
     def kill(self) -> None:
         if self._flusher is None:
@@ -97,7 +115,12 @@ def kill(self) -> None:
         self._flusher = None
 
     def flush(self) -> None:
-        self._flush()
+        was_active = getattr(self._active, "flag", False)
+        self._active.flag = True
+        try:
+            self._flush()
+        finally:
+            self._active.flag = was_active
 
     def _add_to_envelope(self, envelope: "Envelope") -> None:
         envelope.add_item(
diff --git a/sentry_sdk/_log_batcher.py b/sentry_sdk/_log_batcher.py
index 1c59f7379c..d765236846 100644
--- a/sentry_sdk/_log_batcher.py
+++ b/sentry_sdk/_log_batcher.py
@@ -2,7 +2,7 @@
 
 from sentry_sdk._batcher import Batcher
 from sentry_sdk.utils import serialize_attribute
-from sentry_sdk.envelope import Envelope, Item, PayloadRef
+from sentry_sdk.envelope import Item, PayloadRef
 
 if TYPE_CHECKING:
     from typing import Any
diff --git a/sentry_sdk/_metrics_batcher.py b/sentry_sdk/_metrics_batcher.py
index e60a4c86ec..92cece209b 100644
--- a/sentry_sdk/_metrics_batcher.py
+++ b/sentry_sdk/_metrics_batcher.py
@@ -2,7 +2,6 @@
 
 from sentry_sdk._batcher import Batcher
 from sentry_sdk.utils import serialize_attribute
-from sentry_sdk.envelope import Item
 
 if TYPE_CHECKING:
     from typing import Any
diff --git a/sentry_sdk/_span_batcher.py b/sentry_sdk/_span_batcher.py
index df3598b282..967011c083 100644
--- a/sentry_sdk/_span_batcher.py
+++ b/sentry_sdk/_span_batcher.py
@@ -4,14 +4,12 @@
 from typing import TYPE_CHECKING
 
 from sentry_sdk._batcher import Batcher
-from sentry_sdk.consts import SPANSTATUS
 from sentry_sdk.envelope import Envelope, Item, PayloadRef
-from sentry_sdk.utils import format_timestamp, serialize_attribute, safe_repr
+from sentry_sdk.utils import format_timestamp, serialize_attribute
 
 if TYPE_CHECKING:
     from typing import Any, Callable, Optional
     from sentry_sdk.traces import StreamedSpan
-    from sentry_sdk._types import SerializedAttributeValue
 
 
 class SpanBatcher(Batcher["StreamedSpan"]):
@@ -45,6 +43,7 @@ def __init__(
         self._record_lost_func = record_lost_func
         self._running = True
         self._lock = threading.Lock()
+        self._active: "threading.local" = threading.local()
 
         self._flush_event: "threading.Event" = threading.Event()
 
@@ -52,29 +51,42 @@ def __init__(
         self._flusher_pid: "Optional[int]" = None
 
     def add(self, span: "StreamedSpan") -> None:
-        if not self._ensure_thread() or self._flusher is None:
+        # Bail out if the current thread is already executing batcher code.
+        # This prevents deadlocks when code running inside the batcher (e.g.
+        # _add_to_envelope during flush, or _flush_event.wait/set) triggers
+        # a GC-emitted warning that routes back through the logging
+        # integration into add().
+        if getattr(self._active, "flag", False):
             return None
 
-        with self._lock:
-            size = len(self._span_buffer[span.trace_id])
-            if size >= self.MAX_BEFORE_DROP:
-                self._record_lost_func(
-                    reason="queue_overflow",
-                    data_category="span",
-                    quantity=1,
-                )
-                return None
-
-            self._span_buffer[span.trace_id].append(span)
-            self._running_size[span.trace_id] += self._estimate_size(span)
+        self._active.flag = True
 
-            if size + 1 >= self.MAX_BEFORE_FLUSH:
-                self._flush_event.set()
-                return
+        try:
+            if not self._ensure_thread() or self._flusher is None:
+                return None
 
-            if self._running_size[span.trace_id] >= self.MAX_BYTES_BEFORE_FLUSH:
-                self._flush_event.set()
-                return
+            with self._lock:
+                size = len(self._span_buffer[span.trace_id])
+                if size >= self.MAX_BEFORE_DROP:
+                    self._record_lost_func(
+                        reason="queue_overflow",
+                        data_category="span",
+                        quantity=1,
+                    )
+                    return None
+
+                self._span_buffer[span.trace_id].append(span)
+                self._running_size[span.trace_id] += self._estimate_size(span)
+
+                if size + 1 >= self.MAX_BEFORE_FLUSH:
+                    self._flush_event.set()
+                    return
+
+                if self._running_size[span.trace_id] >= self.MAX_BYTES_BEFORE_FLUSH:
+                    self._flush_event.set()
+                    return
+        finally:
+            self._active.flag = False
 
     @staticmethod
     def _estimate_size(item: "StreamedSpan") -> int:
@@ -116,9 +128,7 @@ def _flush(self) -> None:
             envelopes = []
             for trace_id, spans in self._span_buffer.items():
                 if spans:
-                    # TODO[span-first]
-                    # dsc = spans[0].dynamic_sampling_context()
-                    dsc = None
+                    dsc = spans[0]._dynamic_sampling_context()
 
                     # Max per envelope is 1000, so if we happen to have more than
                     # 1000 spans in one bucket, we'll need to separate them.
diff --git a/sentry_sdk/_types.py b/sentry_sdk/_types.py
index e3e8c16f90..baf5f6a2fd 100644
--- a/sentry_sdk/_types.py
+++ b/sentry_sdk/_types.py
@@ -109,7 +109,6 @@ def substituted_because_contains_sensitive_data(cls) -> "AnnotatedValue":
     from typing import Mapping
     from typing import NotRequired
     from typing import Optional
-    from typing import Tuple
     from typing import Type
     from typing_extensions import Literal, TypedDict
 
diff --git a/sentry_sdk/ai/__init__.py b/sentry_sdk/ai/__init__.py
index 7f0d9f92f7..3e5f13727b 100644
--- a/sentry_sdk/ai/__init__.py
+++ b/sentry_sdk/ai/__init__.py
@@ -1,8 +1,8 @@
 from .utils import (
-    set_data_normalized,
-    GEN_AI_MESSAGE_ROLE_MAPPING,
-    GEN_AI_MESSAGE_ROLE_REVERSE_MAPPING,
-    normalize_message_role,
-    normalize_message_roles,
-    set_conversation_id,
-)  # noqa: F401
+    set_data_normalized,  # noqa: F401
+    GEN_AI_MESSAGE_ROLE_MAPPING,  # noqa: F401
+    GEN_AI_MESSAGE_ROLE_REVERSE_MAPPING,  # noqa: F401
+    normalize_message_role,  # noqa: F401
+    normalize_message_roles,  # noqa: F401
+    set_conversation_id,  # noqa: F401
+)
diff --git a/sentry_sdk/ai/utils.py b/sentry_sdk/ai/utils.py
index 5acc501172..3cfae61546 100644
--- a/sentry_sdk/ai/utils.py
+++ b/sentry_sdk/ai/utils.py
@@ -1,8 +1,6 @@
 import inspect
 import json
-from collections import deque
 from copy import deepcopy
-from sys import getsizeof
 from typing import TYPE_CHECKING
 
 from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
@@ -14,6 +12,8 @@
 
 import sentry_sdk
 from sentry_sdk.utils import logger
+from sentry_sdk.traces import StreamedSpan
+from sentry_sdk.tracing_utils import has_span_streaming_enabled
 
 MAX_GEN_AI_MESSAGE_BYTES = 20_000  # 20KB
 # Maximum characters when only a single message is left after bytes truncation
@@ -525,7 +525,14 @@ def normalize_message_roles(messages: "list[dict[str, Any]]") -> "list[dict[str,
 
 
 def get_start_span_function() -> "Callable[..., Any]":
+    if has_span_streaming_enabled(sentry_sdk.get_client().options):
+        return sentry_sdk.traces.start_span
+
     current_span = sentry_sdk.get_current_span()
+    if isinstance(current_span, StreamedSpan):
+        # mypy
+        return sentry_sdk.traces.start_span
+
     transaction_exists = (
         current_span is not None and current_span.containing_transaction is not None
     )
@@ -543,10 +550,25 @@ def _truncate_single_message_content_if_present(
         return message
     content = message["content"]
 
-    if not isinstance(content, str) or len(content) <= max_chars:
+    if isinstance(content, str):
+        if len(content) <= max_chars:
+            return message
+        message["content"] = content[:max_chars] + "..."
+        return message
+
+    if isinstance(content, list):
+        remaining = max_chars
+        for item in content:
+            if isinstance(item, dict) and "text" in item:
+                text = item["text"]
+                if isinstance(text, str):
+                    if len(text) > remaining:
+                        item["text"] = text[:remaining] + "..."
+                        remaining = 0
+                    else:
+                        remaining -= len(text)
         return message
 
-    message["content"] = content[:max_chars] + "..."
     return message
 
 
diff --git a/sentry_sdk/api.py b/sentry_sdk/api.py
index bea22d8be7..a9936230ad 100644
--- a/sentry_sdk/api.py
+++ b/sentry_sdk/api.py
@@ -6,6 +6,7 @@
 from sentry_sdk._init_implementation import init
 from sentry_sdk.consts import INSTRUMENTER
 from sentry_sdk.scope import Scope, _ScopeManager, new_scope, isolation_scope
+from sentry_sdk.traces import StreamedSpan
 from sentry_sdk.tracing import NoOpSpan, Transaction, trace
 from sentry_sdk.crons import monitor
 
@@ -37,6 +38,7 @@
         LogLevelStr,
         SamplingContext,
     )
+    from sentry_sdk.traces import StreamedSpan
     from sentry_sdk.tracing import Span, TransactionKwargs
 
     T = TypeVar("T")
@@ -409,7 +411,9 @@ def set_measurement(name: str, value: float, unit: "MeasurementUnit" = "") -> No
         transaction.set_measurement(name, value, unit)
 
 
-def get_current_span(scope: "Optional[Scope]" = None) -> "Optional[Span]":
+def get_current_span(
+    scope: "Optional[Scope]" = None,
+) -> "Optional[Union[Span, StreamedSpan]]":
     """
     Returns the currently active span if there is one running, otherwise `None`
     """
@@ -525,6 +529,16 @@ def update_current_span(
     if current_span is None:
         return
 
+    if isinstance(current_span, StreamedSpan):
+        warnings.warn(
+            "The `update_current_span` API isn't available in streaming mode. "
+            "Retrieve the current span with get_current_span() and use its API "
+            "directly.",
+            DeprecationWarning,
+            stacklevel=2,
+        )
+        return
+
     if op is not None:
         current_span.op = op
 
diff --git a/sentry_sdk/client.py b/sentry_sdk/client.py
index f540a49f35..9aa26a4f30 100644
--- a/sentry_sdk/client.py
+++ b/sentry_sdk/client.py
@@ -8,8 +8,7 @@
 from typing import TYPE_CHECKING, List, Dict, cast, overload
 import warnings
 
-import sentry_sdk
-from sentry_sdk._compat import PY37, check_uwsgi_thread_support
+from sentry_sdk._compat import check_uwsgi_thread_support
 from sentry_sdk._metrics_batcher import MetricsBatcher
 from sentry_sdk._span_batcher import SpanBatcher
 from sentry_sdk.utils import (
@@ -23,7 +22,6 @@
     get_type_name,
     get_default_release,
     handle_in_app,
-    is_gevent,
     logger,
     get_before_send_log,
     get_before_send_metric,
diff --git a/sentry_sdk/consts.py b/sentry_sdk/consts.py
index eb077ef62f..74769690d7 100644
--- a/sentry_sdk/consts.py
+++ b/sentry_sdk/consts.py
@@ -54,7 +54,6 @@ class CompressionAlgo(Enum):
         Hint,
         IgnoreSpansConfig,
         Log,
-        MeasurementUnit,
         Metric,
         ProfilerMode,
         TracesSampler,
@@ -85,6 +84,7 @@ class CompressionAlgo(Enum):
             "before_send_metric": Optional[Callable[[Metric, Hint], Optional[Metric]]],
             "trace_lifecycle": Optional[Literal["static", "stream"]],
             "ignore_spans": Optional[IgnoreSpansConfig],
+            "suppress_asgi_chained_exceptions": Optional[bool],
         },
         total=False,
     )
@@ -1492,4 +1492,4 @@ def _get_default_options() -> "dict[str, Any]":
 del _get_default_options
 
 
-VERSION = "2.54.0"
+VERSION = "2.56.0"
diff --git a/sentry_sdk/feature_flags.py b/sentry_sdk/feature_flags.py
index c9f3f303f9..de0cefbcad 100644
--- a/sentry_sdk/feature_flags.py
+++ b/sentry_sdk/feature_flags.py
@@ -1,6 +1,7 @@
 import copy
 import sentry_sdk
 from sentry_sdk._lru_cache import LRUCache
+from sentry_sdk.tracing import Span
 from threading import Lock
 
 from typing import TYPE_CHECKING, Any
@@ -61,5 +62,5 @@ def add_feature_flag(flag: str, result: bool) -> None:
     flags.set(flag, result)
 
     span = sentry_sdk.get_current_span()
-    if span:
+    if span and isinstance(span, Span):
         span.set_flag(f"flag.evaluation.{flag}", result)
diff --git a/sentry_sdk/integrations/anthropic.py b/sentry_sdk/integrations/anthropic.py
index eca9e8bd3e..40c1fa0635 100644
--- a/sentry_sdk/integrations/anthropic.py
+++ b/sentry_sdk/integrations/anthropic.py
@@ -37,7 +37,23 @@
     except ImportError:
         Omit = None
 
+    from anthropic import Stream, AsyncStream
     from anthropic.resources import AsyncMessages, Messages
+    from anthropic.lib.streaming import (
+        MessageStreamManager,
+        MessageStream,
+        AsyncMessageStreamManager,
+        AsyncMessageStream,
+    )
+
+    from anthropic.types import (
+        MessageStartEvent,
+        MessageDeltaEvent,
+        MessageStopEvent,
+        ContentBlockStartEvent,
+        ContentBlockDeltaEvent,
+        ContentBlockStopEvent,
+    )
 
     if TYPE_CHECKING:
         from anthropic.types import MessageStreamEvent, TextBlockParam
@@ -45,10 +61,26 @@
     raise DidNotEnable("Anthropic not installed")
 
 if TYPE_CHECKING:
-    from typing import Any, AsyncIterator, Iterator, List, Optional, Union
+    from typing import (
+        Any,
+        AsyncIterator,
+        Iterator,
+        Optional,
+        Union,
+        Callable,
+        Awaitable,
+    )
     from sentry_sdk.tracing import Span
     from sentry_sdk._types import TextPart
 
+    from anthropic.types import (
+        RawMessageStreamEvent,
+        MessageParam,
+        ModelParam,
+        TextBlockParam,
+        ToolUnionParam,
+    )
+
 
 class _RecordedUsage:
     output_tokens: int = 0
@@ -57,6 +89,55 @@ class _RecordedUsage:
     cache_read_input_tokens: "Optional[int]" = 0
 
 
+class _StreamSpanContext:
+    """
+    Sets accumulated data on the stream's span and finishes the span on exit.
+    Is a no-op if the stream has no span set, i.e., when the span has already been finished.
+    """
+
+    def __init__(
+        self,
+        stream: "Union[Stream, MessageStream, AsyncStream, AsyncMessageStream]",
+        # Flag to avoid unreachable branches when the stream state is known to be initialized (stream._model, etc. are set).
+        guaranteed_streaming_state: bool = False,
+    ) -> None:
+        self._stream = stream
+        self._guaranteed_streaming_state = guaranteed_streaming_state
+
+    def __enter__(self) -> "_StreamSpanContext":
+        return self
+
+    def __exit__(
+        self,
+        exc_type: "Optional[type[BaseException]]",
+        exc_val: "Optional[BaseException]",
+        exc_tb: "Optional[Any]",
+    ) -> None:
+        with capture_internal_exceptions():
+            if not hasattr(self._stream, "_span"):
+                return
+
+            if not self._guaranteed_streaming_state and not hasattr(
+                self._stream, "_model"
+            ):
+                self._stream._span.__exit__(exc_type, exc_val, exc_tb)
+                del self._stream._span
+                return
+
+            _set_streaming_output_data(
+                span=self._stream._span,
+                integration=self._stream._integration,
+                model=self._stream._model,
+                usage=self._stream._usage,
+                content_blocks=self._stream._content_blocks,
+                response_id=self._stream._response_id,
+                finish_reason=self._stream._finish_reason,
+            )
+
+            self._stream._span.__exit__(exc_type, exc_val, exc_tb)
+            del self._stream._span
+
+
 class AnthropicIntegration(Integration):
     identifier = "anthropic"
     origin = f"auto.ai.{identifier}"
@@ -69,8 +150,48 @@ def setup_once() -> None:
         version = package_version("anthropic")
         _check_minimum_version(AnthropicIntegration, version)
 
+        """
+        client.messages.create(stream=True) can return an instance of the Stream class, which implements the iterator protocol.
+        Analogously, the function can return an AsyncStream, which implements the asynchronous iterator protocol.
+        The private _iterator variable and the close() method are patched. During iteration over the _iterator generator,
+        information from intercepted events is accumulated and used to populate output attributes on the AI Client Span.
+
+        The span can be finished in two places:
+        - When the user exits the context manager or directly calls close(), the patched close() finishes the span.
+        - When iteration ends, the finally block in the _iterator wrapper finishes the span.
+
+        Both paths may run. For example, the context manager exit can follow iterator exhaustion.
+        """
         Messages.create = _wrap_message_create(Messages.create)
+        Stream.close = _wrap_close(Stream.close)
+
         AsyncMessages.create = _wrap_message_create_async(AsyncMessages.create)
+        AsyncStream.close = _wrap_async_close(AsyncStream.close)
+
+        """
+        client.messages.stream() patches are analogous to the patches for client.messages.create(stream=True) described above.
+        """
+        Messages.stream = _wrap_message_stream(Messages.stream)
+        MessageStreamManager.__enter__ = _wrap_message_stream_manager_enter(
+            MessageStreamManager.__enter__
+        )
+
+        # Before https://github.com/anthropics/anthropic-sdk-python/commit/b1a1c0354a9aca450a7d512fdbdeb59c0ead688a
+        # MessageStream inherits from Stream, so patching Stream is sufficient on these versions.
+        if not issubclass(MessageStream, Stream):
+            MessageStream.close = _wrap_close(MessageStream.close)
+
+        AsyncMessages.stream = _wrap_async_message_stream(AsyncMessages.stream)
+        AsyncMessageStreamManager.__aenter__ = (
+            _wrap_async_message_stream_manager_aenter(
+                AsyncMessageStreamManager.__aenter__
+            )
+        )
+
+        # Before https://github.com/anthropics/anthropic-sdk-python/commit/b1a1c0354a9aca450a7d512fdbdeb59c0ead688a
+        # AsyncMessageStream inherits from AsyncStream, so patching Stream is sufficient on these versions.
+        if not issubclass(AsyncMessageStream, AsyncStream):
+            AsyncMessageStream.close = _wrap_async_close(AsyncMessageStream.close)
 
 
 def _capture_exception(exc: "Any") -> None:
@@ -126,7 +247,9 @@ def _collect_ai_data(
     model: "str | None",
     usage: "_RecordedUsage",
     content_blocks: "list[str]",
-) -> "tuple[str | None, _RecordedUsage, list[str]]":
+    response_id: "str | None" = None,
+    finish_reason: "str | None" = None,
+) -> "tuple[str | None, _RecordedUsage, list[str], str | None, str | None]":
     """
     Collect model information, token usage, and collect content blocks from the AI streaming response.
     """
@@ -146,6 +269,7 @@ def _collect_ai_data(
             # https://github.com/anthropics/anthropic-sdk-python/blob/9c485f6966e10ae0ea9eabb3a921d2ea8145a25b/src/anthropic/lib/streaming/_messages.py#L433-L518
             if event.type == "message_start":
                 model = event.message.model or model
+                response_id = event.message.id
 
                 incoming_usage = event.message.usage
                 usage.output_tokens = incoming_usage.output_tokens
@@ -162,6 +286,8 @@ def _collect_ai_data(
                     model,
                     usage,
                     content_blocks,
+                    response_id,
+                    finish_reason,
                 )
 
             # Counterintuitive, but message_delta contains cumulative token counts :)
@@ -186,16 +312,17 @@ def _collect_ai_data(
                     usage.cache_read_input_tokens = cache_read_input_tokens
                 # TODO: Record event.usage.server_tool_use
 
-                return (
-                    model,
-                    usage,
-                    content_blocks,
-                )
+                if event.delta.stop_reason is not None:
+                    finish_reason = event.delta.stop_reason
+
+                return (model, usage, content_blocks, response_id, finish_reason)
 
     return (
         model,
         usage,
         content_blocks,
+        response_id,
+        finish_reason,
     )
 
 
@@ -241,27 +368,33 @@ def _transform_system_instructions(
     ]
 
 
-def _set_input_data(
-    span: "Span", kwargs: "dict[str, Any]", integration: "AnthropicIntegration"
+def _set_common_input_data(
+    span: "Span",
+    integration: "AnthropicIntegration",
+    max_tokens: "int",
+    messages: "Iterable[MessageParam]",
+    model: "ModelParam",
+    system: "Optional[Union[str, Iterable[TextBlockParam]]]",
+    temperature: "Optional[float]",
+    top_k: "Optional[int]",
+    top_p: "Optional[float]",
+    tools: "Optional[Iterable[ToolUnionParam]]",
 ) -> None:
     """
     Set input data for the span based on the provided keyword arguments for the anthropic message creation.
     """
+    span.set_data(SPANDATA.GEN_AI_SYSTEM, "anthropic")
     span.set_data(SPANDATA.GEN_AI_OPERATION_NAME, "chat")
-    system_instructions: "Union[str, Iterable[TextBlockParam]]" = kwargs.get("system")  # type: ignore
-    messages = kwargs.get("messages")
     if (
         messages is not None
-        and len(messages) > 0
+        and len(messages) > 0  # type: ignore
         and should_send_default_pii()
         and integration.include_prompts
     ):
-        if isinstance(system_instructions, str) or isinstance(
-            system_instructions, Iterable
-        ):
+        if isinstance(system, str) or isinstance(system, Iterable):
             span.set_data(
                 SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS,
-                json.dumps(_transform_system_instructions(system_instructions)),
+                json.dumps(_transform_system_instructions(system)),
             )
 
         normalized_messages = []
@@ -317,25 +450,101 @@ def _set_input_data(
                 span, SPANDATA.GEN_AI_REQUEST_MESSAGES, messages_data, unpack=False
             )
 
+    if max_tokens is not None and _is_given(max_tokens):
+        span.set_data(SPANDATA.GEN_AI_REQUEST_MAX_TOKENS, max_tokens)
+    if model is not None and _is_given(model):
+        span.set_data(SPANDATA.GEN_AI_REQUEST_MODEL, model)
+    if temperature is not None and _is_given(temperature):
+        span.set_data(SPANDATA.GEN_AI_REQUEST_TEMPERATURE, temperature)
+    if top_k is not None and _is_given(top_k):
+        span.set_data(SPANDATA.GEN_AI_REQUEST_TOP_K, top_k)
+    if top_p is not None and _is_given(top_p):
+        span.set_data(SPANDATA.GEN_AI_REQUEST_TOP_P, top_p)
+
+    if tools is not None and _is_given(tools) and len(tools) > 0:  # type: ignore
+        span.set_data(SPANDATA.GEN_AI_REQUEST_AVAILABLE_TOOLS, safe_serialize(tools))
+
+
+def _set_create_input_data(
+    span: "Span", kwargs: "dict[str, Any]", integration: "AnthropicIntegration"
+) -> None:
+    """
+    Set input data for the span based on the provided keyword arguments for the anthropic message creation.
+    """
     span.set_data(SPANDATA.GEN_AI_RESPONSE_STREAMING, kwargs.get("stream", False))
 
-    kwargs_keys_to_attributes = {
-        "max_tokens": SPANDATA.GEN_AI_REQUEST_MAX_TOKENS,
-        "model": SPANDATA.GEN_AI_REQUEST_MODEL,
-        "temperature": SPANDATA.GEN_AI_REQUEST_TEMPERATURE,
-        "top_k": SPANDATA.GEN_AI_REQUEST_TOP_K,
-        "top_p": SPANDATA.GEN_AI_REQUEST_TOP_P,
-    }
-    for key, attribute in kwargs_keys_to_attributes.items():
-        value = kwargs.get(key)
-
-        if value is not None and _is_given(value):
-            span.set_data(attribute, value)
-
-    # Input attributes: Tools
-    tools = kwargs.get("tools")
-    if tools is not None and _is_given(tools) and len(tools) > 0:
-        span.set_data(SPANDATA.GEN_AI_REQUEST_AVAILABLE_TOOLS, safe_serialize(tools))
+    _set_common_input_data(
+        span=span,
+        integration=integration,
+        max_tokens=kwargs.get("max_tokens"),  # type: ignore
+        messages=kwargs.get("messages"),  # type: ignore
+        model=kwargs.get("model"),
+        system=kwargs.get("system"),
+        temperature=kwargs.get("temperature"),
+        top_k=kwargs.get("top_k"),
+        top_p=kwargs.get("top_p"),
+        tools=kwargs.get("tools"),
+    )
+
+
+def _wrap_synchronous_message_iterator(
+    stream: "Union[Stream, MessageStream]",
+    iterator: "Iterator[Union[RawMessageStreamEvent, MessageStreamEvent]]",
+) -> "Iterator[Union[RawMessageStreamEvent, MessageStreamEvent]]":
+    """
+    Sets information received while iterating the response stream on the AI Client Span.
+    Responsible for closing the AI Client Span unless the span has already been closed in the close() patch.
+    """
+    with _StreamSpanContext(stream, guaranteed_streaming_state=True):
+        for event in iterator:
+            # Message and content types are aliases for corresponding Raw* types, introduced in
+            # https://github.com/anthropics/anthropic-sdk-python/commit/bc9d11cd2addec6976c46db10b7c89a8c276101a
+            if not isinstance(
+                event,
+                (
+                    MessageStartEvent,
+                    MessageDeltaEvent,
+                    MessageStopEvent,
+                    ContentBlockStartEvent,
+                    ContentBlockDeltaEvent,
+                    ContentBlockStopEvent,
+                ),
+            ):
+                yield event
+                continue
+
+            _accumulate_event_data(stream, event)
+            yield event
+
+
+async def _wrap_asynchronous_message_iterator(
+    stream: "Union[AsyncStream, AsyncMessageStream]",
+    iterator: "AsyncIterator[Union[RawMessageStreamEvent, MessageStreamEvent]]",
+) -> "AsyncIterator[Union[RawMessageStreamEvent, MessageStreamEvent]]":
+    """
+    Sets information received while iterating the response stream on the AI Client Span.
+    Responsible for closing the AI Client Span unless the span has already been closed in the close() patch.
+    """
+    with _StreamSpanContext(stream, guaranteed_streaming_state=True):
+        async for event in iterator:
+            # Message and content types are aliases for corresponding Raw* types, introduced in
+            # https://github.com/anthropics/anthropic-sdk-python/commit/bc9d11cd2addec6976c46db10b7c89a8c276101a
+            if not isinstance(
+                event,
+                (
+                    MessageStartEvent,
+                    MessageDeltaEvent,
+                    MessageStopEvent,
+                    ContentBlockStartEvent,
+                    ContentBlockDeltaEvent,
+                    ContentBlockStopEvent,
+                ),
+            ):
+                yield event
+                continue
+
+            _accumulate_event_data(stream, event)
+            yield event
 
 
 def _set_output_data(
@@ -347,11 +556,16 @@ def _set_output_data(
     cache_read_input_tokens: "int | None",
     cache_write_input_tokens: "int | None",
     content_blocks: "list[Any]",
-    finish_span: bool = False,
+    response_id: "str | None" = None,
+    finish_reason: "str | None" = None,
 ) -> None:
     """
     Set output data for the span based on the AI response."""
     span.set_data(SPANDATA.GEN_AI_RESPONSE_MODEL, model)
+    if response_id is not None:
+        span.set_data(SPANDATA.GEN_AI_RESPONSE_ID, response_id)
+    if finish_reason is not None:
+        span.set_data(SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS, [finish_reason])
     if should_send_default_pii() and integration.include_prompts:
         output_messages: "dict[str, list[Any]]" = {
             "response": [],
@@ -385,9 +599,6 @@ def _set_output_data(
         input_tokens_cache_write=cache_write_input_tokens,
     )
 
-    if finish_span:
-        span.__exit__(None, None, None)
-
 
 def _sentry_patched_create_common(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
     integration = kwargs.pop("integration")
@@ -411,10 +622,34 @@ def _sentry_patched_create_common(f: "Any", *args: "Any", **kwargs: "Any") -> "A
     )
     span.__enter__()
 
-    _set_input_data(span, kwargs, integration)
+    _set_create_input_data(span, kwargs, integration)
 
     result = yield f, args, kwargs
 
+    if isinstance(result, Stream):
+        result._span = span
+        result._integration = integration
+
+        _initialize_data_accumulation_state(result)
+        result._iterator = _wrap_synchronous_message_iterator(
+            result,
+            result._iterator,
+        )
+
+        return result
+
+    if isinstance(result, AsyncStream):
+        result._span = span
+        result._integration = integration
+
+        _initialize_data_accumulation_state(result)
+        result._iterator = _wrap_asynchronous_message_iterator(
+            result,
+            result._iterator,
+        )
+
+        return result
+
     with capture_internal_exceptions():
         if hasattr(result, "content"):
             (
@@ -442,94 +677,10 @@ def _sentry_patched_create_common(f: "Any", *args: "Any", **kwargs: "Any") -> "A
                 cache_read_input_tokens=cache_read_input_tokens,
                 cache_write_input_tokens=cache_write_input_tokens,
                 content_blocks=content_blocks,
-                finish_span=True,
+                response_id=getattr(result, "id", None),
+                finish_reason=getattr(result, "stop_reason", None),
             )
-
-        # Streaming response
-        elif hasattr(result, "_iterator"):
-            old_iterator = result._iterator
-
-            def new_iterator() -> "Iterator[MessageStreamEvent]":
-                model = None
-                usage = _RecordedUsage()
-                content_blocks: "list[str]" = []
-
-                for event in old_iterator:
-                    (
-                        model,
-                        usage,
-                        content_blocks,
-                    ) = _collect_ai_data(
-                        event,
-                        model,
-                        usage,
-                        content_blocks,
-                    )
-                    yield event
-
-                # Anthropic's input_tokens excludes cached/cache_write tokens.
-                # Normalize to total input tokens for correct cost calculations.
-                total_input = (
-                    usage.input_tokens
-                    + (usage.cache_read_input_tokens or 0)
-                    + (usage.cache_write_input_tokens or 0)
-                )
-
-                _set_output_data(
-                    span=span,
-                    integration=integration,
-                    model=model,
-                    input_tokens=total_input,
-                    output_tokens=usage.output_tokens,
-                    cache_read_input_tokens=usage.cache_read_input_tokens,
-                    cache_write_input_tokens=usage.cache_write_input_tokens,
-                    content_blocks=[{"text": "".join(content_blocks), "type": "text"}],
-                    finish_span=True,
-                )
-
-            async def new_iterator_async() -> "AsyncIterator[MessageStreamEvent]":
-                model = None
-                usage = _RecordedUsage()
-                content_blocks: "list[str]" = []
-
-                async for event in old_iterator:
-                    (
-                        model,
-                        usage,
-                        content_blocks,
-                    ) = _collect_ai_data(
-                        event,
-                        model,
-                        usage,
-                        content_blocks,
-                    )
-                    yield event
-
-                # Anthropic's input_tokens excludes cached/cache_write tokens.
-                # Normalize to total input tokens for correct cost calculations.
-                total_input = (
-                    usage.input_tokens
-                    + (usage.cache_read_input_tokens or 0)
-                    + (usage.cache_write_input_tokens or 0)
-                )
-
-                _set_output_data(
-                    span=span,
-                    integration=integration,
-                    model=model,
-                    input_tokens=total_input,
-                    output_tokens=usage.output_tokens,
-                    cache_read_input_tokens=usage.cache_read_input_tokens,
-                    cache_write_input_tokens=usage.cache_write_input_tokens,
-                    content_blocks=[{"text": "".join(content_blocks), "type": "text"}],
-                    finish_span=True,
-                )
-
-            if str(type(result._iterator)) == "<class 'async_generator'>":
-                result._iterator = new_iterator_async()
-            else:
-                result._iterator = new_iterator()
-
+            span.__exit__(None, None, None)
         else:
             span.set_data("unknown_response", True)
             span.__exit__(None, None, None)
@@ -575,6 +726,89 @@ def _sentry_patched_create_sync(*args: "Any", **kwargs: "Any") -> "Any":
     return _sentry_patched_create_sync
 
 
+def _initialize_data_accumulation_state(stream: "Union[Stream, MessageStream]") -> None:
+    """
+    Initialize fields for accumulating output on the Stream instance.
+    """
+    if not hasattr(stream, "_model"):
+        stream._model = None
+        stream._usage = _RecordedUsage()
+        stream._content_blocks = []
+        stream._response_id = None
+        stream._finish_reason = None
+
+
+def _accumulate_event_data(
+    stream: "Union[Stream, MessageStream]",
+    event: "Union[RawMessageStreamEvent, MessageStreamEvent]",
+) -> None:
+    """
+    Update accumulated output from a single stream event.
+    """
+    (model, usage, content_blocks, response_id, finish_reason) = _collect_ai_data(
+        event,
+        stream._model,
+        stream._usage,
+        stream._content_blocks,
+        stream._response_id,
+        stream._finish_reason,
+    )
+
+    stream._model = model
+    stream._usage = usage
+    stream._content_blocks = content_blocks
+    stream._response_id = response_id
+    stream._finish_reason = finish_reason
+
+
+def _set_streaming_output_data(
+    span: "Span",
+    integration: "AnthropicIntegration",
+    model: "Optional[str]",
+    usage: "_RecordedUsage",
+    content_blocks: "list[str]",
+    response_id: "Optional[str]",
+    finish_reason: "Optional[str]",
+) -> None:
+    """
+    Set output attributes on the AI Client Span.
+    """
+    # Anthropic's input_tokens excludes cached/cache_write tokens.
+    # Normalize to total input tokens for correct cost calculations.
+    total_input = (
+        usage.input_tokens
+        + (usage.cache_read_input_tokens or 0)
+        + (usage.cache_write_input_tokens or 0)
+    )
+
+    _set_output_data(
+        span=span,
+        integration=integration,
+        model=model,
+        input_tokens=total_input,
+        output_tokens=usage.output_tokens,
+        cache_read_input_tokens=usage.cache_read_input_tokens,
+        cache_write_input_tokens=usage.cache_write_input_tokens,
+        content_blocks=[{"text": "".join(content_blocks), "type": "text"}],
+        response_id=response_id,
+        finish_reason=finish_reason,
+    )
+
+
+def _wrap_close(
+    f: "Callable[..., None]",
+) -> "Callable[..., None]":
+    """
+    Closes the AI Client Span unless the finally block in `_wrap_synchronous_message_iterator()` runs first.
+    """
+
+    def close(self: "Union[Stream, MessageStream]") -> None:
+        with _StreamSpanContext(self):
+            return f(self)
+
+    return close
+
+
 def _wrap_message_create_async(f: "Any") -> "Any":
     async def _execute_async(f: "Any", *args: "Any", **kwargs: "Any") -> "Any":
         gen = _sentry_patched_create_common(f, *args, **kwargs)
@@ -613,6 +847,190 @@ async def _sentry_patched_create_async(*args: "Any", **kwargs: "Any") -> "Any":
     return _sentry_patched_create_async
 
 
+def _wrap_async_close(
+    f: "Callable[..., Awaitable[None]]",
+) -> "Callable[..., Awaitable[None]]":
+    """
+    Closes the AI Client Span unless the finally block in `_wrap_asynchronous_message_iterator()` runs first.
+    """
+
+    async def close(self: "AsyncStream") -> None:
+        with _StreamSpanContext(self):
+            return await f(self)
+
+    return close
+
+
+def _wrap_message_stream(f: "Any") -> "Any":
+    """
+    Attaches user-provided arguments to the returned context manager.
+    The attributes are set on AI Client Spans in the patch for the context manager.
+    """
+
+    @wraps(f)
+    def _sentry_patched_stream(*args: "Any", **kwargs: "Any") -> "MessageStreamManager":
+        stream_manager = f(*args, **kwargs)
+
+        stream_manager._max_tokens = kwargs.get("max_tokens")
+        stream_manager._messages = kwargs.get("messages")
+        stream_manager._model = kwargs.get("model")
+        stream_manager._system = kwargs.get("system")
+        stream_manager._temperature = kwargs.get("temperature")
+        stream_manager._top_k = kwargs.get("top_k")
+        stream_manager._top_p = kwargs.get("top_p")
+        stream_manager._tools = kwargs.get("tools")
+
+        return stream_manager
+
+    return _sentry_patched_stream
+
+
+def _wrap_message_stream_manager_enter(f: "Any") -> "Any":
+    """
+    Creates and manages AI Client Spans.
+    """
+
+    @wraps(f)
+    def _sentry_patched_enter(self: "MessageStreamManager") -> "MessageStream":
+        stream = f(self)
+        if not hasattr(self, "_max_tokens"):
+            return stream
+
+        integration = sentry_sdk.get_client().get_integration(AnthropicIntegration)
+
+        if integration is None:
+            return stream
+
+        if self._messages is None:
+            return stream
+
+        try:
+            iter(self._messages)
+        except TypeError:
+            return stream
+
+        span = get_start_span_function()(
+            op=OP.GEN_AI_CHAT,
+            name="chat" if self._model is None else f"chat {self._model}".strip(),
+            origin=AnthropicIntegration.origin,
+        )
+        span.__enter__()
+
+        span.set_data(SPANDATA.GEN_AI_RESPONSE_STREAMING, True)
+        _set_common_input_data(
+            span=span,
+            integration=integration,
+            max_tokens=self._max_tokens,
+            messages=self._messages,
+            model=self._model,
+            system=self._system,
+            temperature=self._temperature,
+            top_k=self._top_k,
+            top_p=self._top_p,
+            tools=self._tools,
+        )
+
+        stream._span = span
+        stream._integration = integration
+
+        _initialize_data_accumulation_state(stream)
+        stream._iterator = _wrap_synchronous_message_iterator(
+            stream,
+            stream._iterator,
+        )
+
+        return stream
+
+    return _sentry_patched_enter
+
+
+def _wrap_async_message_stream(f: "Any") -> "Any":
+    """
+    Attaches user-provided arguments to the returned context manager.
+    The attributes are set on AI Client Spans in the patch for the context manager.
+    """
+
+    @wraps(f)
+    def _sentry_patched_stream(
+        *args: "Any", **kwargs: "Any"
+    ) -> "AsyncMessageStreamManager":
+        stream_manager = f(*args, **kwargs)
+
+        stream_manager._max_tokens = kwargs.get("max_tokens")
+        stream_manager._messages = kwargs.get("messages")
+        stream_manager._model = kwargs.get("model")
+        stream_manager._system = kwargs.get("system")
+        stream_manager._temperature = kwargs.get("temperature")
+        stream_manager._top_k = kwargs.get("top_k")
+        stream_manager._top_p = kwargs.get("top_p")
+        stream_manager._tools = kwargs.get("tools")
+
+        return stream_manager
+
+    return _sentry_patched_stream
+
+
+def _wrap_async_message_stream_manager_aenter(f: "Any") -> "Any":
+    """
+    Creates and manages AI Client Spans.
+    """
+
+    @wraps(f)
+    async def _sentry_patched_aenter(
+        self: "AsyncMessageStreamManager",
+    ) -> "AsyncMessageStream":
+        stream = await f(self)
+        if not hasattr(self, "_max_tokens"):
+            return stream
+
+        integration = sentry_sdk.get_client().get_integration(AnthropicIntegration)
+
+        if integration is None:
+            return stream
+
+        if self._messages is None:
+            return stream
+
+        try:
+            iter(self._messages)
+        except TypeError:
+            return stream
+
+        span = get_start_span_function()(
+            op=OP.GEN_AI_CHAT,
+            name="chat" if self._model is None else f"chat {self._model}".strip(),
+            origin=AnthropicIntegration.origin,
+        )
+        span.__enter__()
+
+        span.set_data(SPANDATA.GEN_AI_RESPONSE_STREAMING, True)
+        _set_common_input_data(
+            span=span,
+            integration=integration,
+            max_tokens=self._max_tokens,
+            messages=self._messages,
+            model=self._model,
+            system=self._system,
+            temperature=self._temperature,
+            top_k=self._top_k,
+            top_p=self._top_p,
+            tools=self._tools,
+        )
+
+        stream._span = span
+        stream._integration = integration
+
+        _initialize_data_accumulation_state(stream)
+        stream._iterator = _wrap_asynchronous_message_iterator(
+            stream,
+            stream._iterator,
+        )
+
+        return stream
+
+    return _sentry_patched_aenter
+
+
 def _is_given(obj: "Any") -> bool:
     """
     Check for givenness safely across different anthropic versions.
diff --git a/sentry_sdk/integrations/asgi.py b/sentry_sdk/integrations/asgi.py
index 6983af89ed..2294781f05 100644
--- a/sentry_sdk/integrations/asgi.py
+++ b/sentry_sdk/integrations/asgi.py
@@ -4,6 +4,7 @@
 Based on Tom Christie's `sentry-asgi <https://github.com/encode/sentry-asgi>`.
 """
 
+import sys
 import asyncio
 import inspect
 from copy import deepcopy
@@ -22,10 +23,13 @@
     nullcontext,
 )
 from sentry_sdk.sessions import track_session
+from sentry_sdk.traces import StreamedSpan
 from sentry_sdk.tracing import (
     SOURCE_FOR_STYLE,
+    Transaction,
     TransactionSource,
 )
+from sentry_sdk.tracing_utils import has_span_streaming_enabled
 from sentry_sdk.utils import (
     ContextVar,
     event_from_exception,
@@ -34,18 +38,22 @@
     logger,
     transaction_from_function,
     _get_installed_modules,
+    reraise,
+    capture_internal_exceptions,
 )
-from sentry_sdk.tracing import Transaction
 
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
     from typing import Any
+    from typing import ContextManager
     from typing import Dict
     from typing import Optional
     from typing import Tuple
+    from typing import Union
 
-    from sentry_sdk._types import Event, Hint
+    from sentry_sdk._types import Attributes, Event, Hint
+    from sentry_sdk.tracing import Span
 
 
 _asgi_middleware_applied = ContextVar("sentry_asgi_middleware_applied")
@@ -182,8 +190,22 @@ async def _run_app(
                     return await self.app(scope, receive, send)
 
             except Exception as exc:
-                self._capture_lifespan_exception(exc)
-                raise exc from None
+                suppress_chained_exceptions = (
+                    sentry_sdk.get_client()
+                    .options.get("_experiments", {})
+                    .get("suppress_asgi_chained_exceptions", True)
+                )
+                if suppress_chained_exceptions:
+                    self._capture_lifespan_exception(exc)
+                    raise exc from None
+
+                exc_info = sys.exc_info()
+                with capture_internal_exceptions():
+                    self._capture_lifespan_exception(exc)
+                reraise(*exc_info)
+
+        client = sentry_sdk.get_client()
+        span_streaming = has_span_streaming_enabled(client.options)
 
         _asgi_middleware_applied.set(True)
         try:
@@ -204,48 +226,105 @@ async def _run_app(
                     )
 
                     method = scope.get("method", "").upper()
-                    transaction = None
-                    if ty in ("http", "websocket"):
-                        if ty == "websocket" or method in self.http_methods_to_capture:
-                            transaction = continue_trace(
-                                _get_headers(scope),
-                                op="{}.server".format(ty),
+
+                    span_ctx: "ContextManager[Union[Span, StreamedSpan, None]]"
+                    if span_streaming:
+                        segment: "Optional[StreamedSpan]" = None
+                        attributes: "Attributes" = {
+                            "sentry.span.source": getattr(
+                                transaction_source, "value", transaction_source
+                            ),
+                            "sentry.origin": self.span_origin,
+                            "asgi.type": ty,
+                        }
+
+                        if ty in ("http", "websocket"):
+                            if (
+                                ty == "websocket"
+                                or method in self.http_methods_to_capture
+                            ):
+                                sentry_sdk.traces.continue_trace(_get_headers(scope))
+
+                                sentry_scope.set_custom_sampling_context(
+                                    {"asgi_scope": scope}
+                                )
+
+                                attributes["sentry.op"] = f"{ty}.server"
+                                segment = sentry_sdk.traces.start_span(
+                                    name=transaction_name, attributes=attributes
+                                )
+                        else:
+                            sentry_sdk.traces.new_trace()
+
+                            sentry_scope.set_custom_sampling_context(
+                                {"asgi_scope": scope}
+                            )
+
+                            attributes["sentry.op"] = OP.HTTP_SERVER
+                            segment = sentry_sdk.traces.start_span(
+                                name=transaction_name, attributes=attributes
+                            )
+
+                        span_ctx = segment or nullcontext()
+
+                    else:
+                        transaction = None
+                        if ty in ("http", "websocket"):
+                            if (
+                                ty == "websocket"
+                                or method in self.http_methods_to_capture
+                            ):
+                                transaction = continue_trace(
+                                    _get_headers(scope),
+                                    op="{}.server".format(ty),
+                                    name=transaction_name,
+                                    source=transaction_source,
+                                    origin=self.span_origin,
+                                )
+                        else:
+                            transaction = Transaction(
+                                op=OP.HTTP_SERVER,
                                 name=transaction_name,
                                 source=transaction_source,
                                 origin=self.span_origin,
                             )
-                    else:
-                        transaction = Transaction(
-                            op=OP.HTTP_SERVER,
-                            name=transaction_name,
-                            source=transaction_source,
-                            origin=self.span_origin,
-                        )
 
-                    if transaction:
-                        transaction.set_tag("asgi.type", ty)
+                        if transaction:
+                            transaction.set_tag("asgi.type", ty)
 
-                    transaction_context = (
-                        sentry_sdk.start_transaction(
-                            transaction,
-                            custom_sampling_context={"asgi_scope": scope},
+                        span_ctx = (
+                            sentry_sdk.start_transaction(
+                                transaction,
+                                custom_sampling_context={"asgi_scope": scope},
+                            )
+                            if transaction is not None
+                            else nullcontext()
                         )
-                        if transaction is not None
-                        else nullcontext()
-                    )
-                    with transaction_context:
+
+                    with span_ctx as span:
                         try:
 
                             async def _sentry_wrapped_send(
                                 event: "Dict[str, Any]",
                             ) -> "Any":
-                                if transaction is not None:
+                                if span is not None:
                                     is_http_response = (
                                         event.get("type") == "http.response.start"
                                         and "status" in event
                                     )
                                     if is_http_response:
-                                        transaction.set_http_status(event["status"])
+                                        if isinstance(span, StreamedSpan):
+                                            span.status = (
+                                                "error"
+                                                if event["status"] >= 400
+                                                else "ok"
+                                            )
+                                            span.set_attribute(
+                                                "http.response.status_code",
+                                                event["status"],
+                                            )
+                                        else:
+                                            span.set_http_status(event["status"])
 
                                 return await send(event)
 
@@ -258,8 +337,19 @@ async def _sentry_wrapped_send(
                                     scope, receive, _sentry_wrapped_send
                                 )
                         except Exception as exc:
-                            self._capture_request_exception(exc)
-                            raise exc from None
+                            suppress_chained_exceptions = (
+                                sentry_sdk.get_client()
+                                .options.get("_experiments", {})
+                                .get("suppress_asgi_chained_exceptions", True)
+                            )
+                            if suppress_chained_exceptions:
+                                self._capture_request_exception(exc)
+                                raise exc from None
+
+                            exc_info = sys.exc_info()
+                            with capture_internal_exceptions():
+                                self._capture_request_exception(exc)
+                            reraise(*exc_info)
         finally:
             _asgi_middleware_applied.set(False)
 
diff --git a/sentry_sdk/integrations/asyncpg.py b/sentry_sdk/integrations/asyncpg.py
index 7f3591154a..d1cf6fcc92 100644
--- a/sentry_sdk/integrations/asyncpg.py
+++ b/sentry_sdk/integrations/asyncpg.py
@@ -1,5 +1,6 @@
 from __future__ import annotations
 import contextlib
+import re
 from typing import Any, TypeVar, Callable, Awaitable, Iterator
 
 import sentry_sdk
@@ -55,6 +56,10 @@ def setup_once() -> None:
 T = TypeVar("T")
 
 
+def _normalize_query(query: str) -> str:
+    return re.sub(r"\s+", " ", query).strip()
+
+
 def _wrap_execute(f: "Callable[..., Awaitable[T]]") -> "Callable[..., Awaitable[T]]":
     async def _inner(*args: "Any", **kwargs: "Any") -> "T":
         if sentry_sdk.get_client().get_integration(AsyncPGIntegration) is None:
@@ -67,7 +72,7 @@ async def _inner(*args: "Any", **kwargs: "Any") -> "T":
         if len(args) > 2:
             return await f(*args, **kwargs)
 
-        query = args[1]
+        query = _normalize_query(args[1])
         with record_sql_queries(
             cursor=None,
             query=query,
@@ -103,6 +108,7 @@ def _record(
 
     param_style = "pyformat" if params_list else None
 
+    query = _normalize_query(query)
     with record_sql_queries(
         cursor=cursor,
         query=query,
diff --git a/sentry_sdk/integrations/celery/__init__.py b/sentry_sdk/integrations/celery/__init__.py
index fe832f159e..b8b1691979 100644
--- a/sentry_sdk/integrations/celery/__init__.py
+++ b/sentry_sdk/integrations/celery/__init__.py
@@ -14,7 +14,7 @@
 )
 from sentry_sdk.integrations.celery.utils import _now_seconds_since_epoch
 from sentry_sdk.integrations.logging import ignore_logger
-from sentry_sdk.tracing import BAGGAGE_HEADER_NAME, TransactionSource
+from sentry_sdk.tracing import BAGGAGE_HEADER_NAME, Span, TransactionSource
 from sentry_sdk.tracing_utils import Baggage
 from sentry_sdk.utils import (
     capture_internal_exceptions,
@@ -34,7 +34,6 @@
     from typing import Union
 
     from sentry_sdk._types import EventProcessor, Event, Hint, ExcInfo
-    from sentry_sdk.tracing import Span
 
     F = TypeVar("F", bound=Callable[..., Any])
 
@@ -100,7 +99,10 @@ def _set_status(status: str) -> None:
     with capture_internal_exceptions():
         scope = sentry_sdk.get_current_scope()
         if scope.span is not None:
-            scope.span.set_status(status)
+            if isinstance(scope.span, Span):
+                scope.span.set_status(status)
+            else:
+                scope.span.status = "ok" if status == "ok" else "error"
 
 
 def _capture_exception(task: "Any", exc_info: "ExcInfo") -> None:
diff --git a/sentry_sdk/integrations/django/tasks.py b/sentry_sdk/integrations/django/tasks.py
index 84bc4d2396..e6adb914e8 100644
--- a/sentry_sdk/integrations/django/tasks.py
+++ b/sentry_sdk/integrations/django/tasks.py
@@ -2,12 +2,11 @@
 
 import sentry_sdk
 from sentry_sdk.consts import OP
-from sentry_sdk.tracing import SPANSTATUS
 from sentry_sdk.utils import qualname_from_function
 
 try:
     # django.tasks were added in Django 6.0
-    from django.tasks.base import Task, TaskResultStatus
+    from django.tasks.base import Task
 except ImportError:
     Task = None
 
diff --git a/sentry_sdk/integrations/google_genai/streaming.py b/sentry_sdk/integrations/google_genai/streaming.py
index 8649ce2ac0..3405fe2b2a 100644
--- a/sentry_sdk/integrations/google_genai/streaming.py
+++ b/sentry_sdk/integrations/google_genai/streaming.py
@@ -1,4 +1,4 @@
-from typing import TYPE_CHECKING, Any, List, TypedDict, Optional, Union
+from typing import TYPE_CHECKING, Any, List, TypedDict, Optional
 
 from sentry_sdk.ai.utils import set_data_normalized
 from sentry_sdk.consts import SPANDATA
diff --git a/sentry_sdk/integrations/google_genai/utils.py b/sentry_sdk/integrations/google_genai/utils.py
index b2d6499843..da7218f282 100644
--- a/sentry_sdk/integrations/google_genai/utils.py
+++ b/sentry_sdk/integrations/google_genai/utils.py
@@ -5,7 +5,6 @@
 from .consts import ORIGIN, TOOL_ATTRIBUTES_MAP, GEN_AI_SYSTEM
 from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
 from typing import (
-    cast,
     TYPE_CHECKING,
     Iterable,
     Any,
@@ -22,7 +21,6 @@
     set_data_normalized,
     truncate_and_annotate_messages,
     normalize_message_roles,
-    redact_blob_message_parts,
     transform_google_content_part,
     get_modality_from_mime_type,
 )
@@ -695,7 +693,7 @@ def _extract_response_text(
 
     texts = []
     for candidate in response.candidates:
-        if not hasattr(candidate, "content") or not hasattr(candidate.content, "parts"):
+        if not hasattr(candidate, "content") or not candidate.content.parts:
             continue
 
         for part in candidate.content.parts:
diff --git a/sentry_sdk/integrations/grpc/aio/server.py b/sentry_sdk/integrations/grpc/aio/server.py
index 3ed15c2de6..1e9eac8920 100644
--- a/sentry_sdk/integrations/grpc/aio/server.py
+++ b/sentry_sdk/integrations/grpc/aio/server.py
@@ -2,7 +2,7 @@
 from sentry_sdk.consts import OP
 from sentry_sdk.integrations import DidNotEnable
 from sentry_sdk.integrations.grpc.consts import SPAN_ORIGIN
-from sentry_sdk.tracing import Transaction, TransactionSource
+from sentry_sdk.tracing import TransactionSource
 from sentry_sdk.utils import event_from_exception
 
 from typing import TYPE_CHECKING
diff --git a/sentry_sdk/integrations/grpc/server.py b/sentry_sdk/integrations/grpc/server.py
index 7c06fd405a..af01f37fb2 100644
--- a/sentry_sdk/integrations/grpc/server.py
+++ b/sentry_sdk/integrations/grpc/server.py
@@ -2,7 +2,7 @@
 from sentry_sdk.consts import OP
 from sentry_sdk.integrations import DidNotEnable
 from sentry_sdk.integrations.grpc.consts import SPAN_ORIGIN
-from sentry_sdk.tracing import Transaction, TransactionSource
+from sentry_sdk.tracing import TransactionSource
 
 from typing import TYPE_CHECKING
 
diff --git a/sentry_sdk/integrations/langchain.py b/sentry_sdk/integrations/langchain.py
index 7a5e863e4d..2c93e4d76e 100644
--- a/sentry_sdk/integrations/langchain.py
+++ b/sentry_sdk/integrations/langchain.py
@@ -108,6 +108,15 @@
     OllamaEmbeddings = None
 
 
+def _get_ai_system(all_params: "Dict[str, Any]") -> "Optional[str]":
+    ai_type = all_params.get("_type")
+
+    if not ai_type or not isinstance(ai_type, str):
+        return None
+
+    return ai_type
+
+
 DATA_FIELDS = {
     "frequency_penalty": SPANDATA.GEN_AI_REQUEST_FREQUENCY_PENALTY,
     "function_call": SPANDATA.GEN_AI_RESPONSE_TOOL_CALLS,
@@ -351,7 +360,6 @@ def on_llm_start(
         metadata: "Optional[Dict[str, Any]]" = None,
         **kwargs: "Any",
     ) -> "Any":
-        """Run when LLM starts running."""
         with capture_internal_exceptions():
             if not run_id:
                 return
@@ -369,23 +377,27 @@ def on_llm_start(
             watched_span = self._create_span(
                 run_id,
                 parent_run_id,
-                op=OP.GEN_AI_PIPELINE,
-                name=kwargs.get("name") or "Langchain LLM call",
+                op=OP.GEN_AI_GENERATE_TEXT,
+                name=f"generate_text {model}".strip(),
                 origin=LangchainIntegration.origin,
             )
             span = watched_span.span
 
+            span.set_data(SPANDATA.GEN_AI_OPERATION_NAME, "generate_text")
+
+            pipeline_name = kwargs.get("name")
+            if pipeline_name:
+                span.set_data(SPANDATA.GEN_AI_PIPELINE_NAME, pipeline_name)
+
             if model:
                 span.set_data(
                     SPANDATA.GEN_AI_REQUEST_MODEL,
                     model,
                 )
 
-            ai_type = all_params.get("_type", "")
-            if "anthropic" in ai_type:
-                span.set_data(SPANDATA.GEN_AI_SYSTEM, "anthropic")
-            elif "openai" in ai_type:
-                span.set_data(SPANDATA.GEN_AI_SYSTEM, "openai")
+            ai_system = _get_ai_system(all_params)
+            if ai_system:
+                span.set_data(SPANDATA.GEN_AI_SYSTEM, ai_system)
 
             for key, attribute in DATA_FIELDS.items():
                 if key in all_params and all_params[key] is not None:
@@ -449,11 +461,9 @@ def on_chat_model_start(
             if model:
                 span.set_data(SPANDATA.GEN_AI_REQUEST_MODEL, model)
 
-            ai_type = all_params.get("_type", "")
-            if "anthropic" in ai_type:
-                span.set_data(SPANDATA.GEN_AI_SYSTEM, "anthropic")
-            elif "openai" in ai_type:
-                span.set_data(SPANDATA.GEN_AI_SYSTEM, "openai")
+            ai_system = _get_ai_system(all_params)
+            if ai_system:
+                span.set_data(SPANDATA.GEN_AI_SYSTEM, ai_system)
 
             agent_name = _get_current_agent()
             if agent_name:
@@ -554,7 +564,8 @@ def on_llm_end(
                     finish_reason = generation.generation_info.get("finish_reason")
                     if finish_reason is not None:
                         span.set_data(
-                            SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS, finish_reason
+                            SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS,
+                            [finish_reason],
                         )
                 except AttributeError:
                     pass
diff --git a/sentry_sdk/integrations/logging.py b/sentry_sdk/integrations/logging.py
index 42029c5a7a..ca13afc1e9 100644
--- a/sentry_sdk/integrations/logging.py
+++ b/sentry_sdk/integrations/logging.py
@@ -54,10 +54,18 @@
 #
 # Note: Ignoring by logger name here is better than mucking with thread-locals.
 # We do not necessarily know whether thread-locals work 100% correctly in the user's environment.
+#
+# Events/breadcrumbs and Sentry Logs have separate ignore lists so that
+# framework loggers silenced for events (e.g. django.server) can still be
+# captured as Sentry Logs.
 _IGNORED_LOGGERS = set(
     ["sentry_sdk.errors", "urllib3.connectionpool", "urllib3.connection"]
 )
 
+_IGNORED_LOGGERS_SENTRY_LOGS = set(
+    ["sentry_sdk.errors", "urllib3.connectionpool", "urllib3.connection"]
+)
+
 
 def ignore_logger(
     name: str,
@@ -67,11 +75,47 @@ def ignore_logger(
     use this to prevent their actions being recorded as breadcrumbs. Exposed
     to users as a way to quiet spammy loggers.
 
+    This does **not** affect Sentry Logs — use
+    :py:func:`ignore_logger_for_sentry_logs` for that.
+
     :param name: The name of the logger to ignore (same string you would pass to ``logging.getLogger``).
     """
     _IGNORED_LOGGERS.add(name)
 
 
+def ignore_logger_for_sentry_logs(
+    name: str,
+) -> None:
+    """This disables recording as Sentry Logs calls to a logger of a
+    specific name.
+
+    :param name: The name of the logger to ignore (same string you would pass to ``logging.getLogger``).
+    """
+    _IGNORED_LOGGERS_SENTRY_LOGS.add(name)
+
+
+def unignore_logger(
+    name: str,
+) -> None:
+    """Reverts a previous :py:func:`ignore_logger` call, re-enabling
+    recording of breadcrumbs and events for the named logger.
+
+    :param name: The name of the logger to unignore.
+    """
+    _IGNORED_LOGGERS.discard(name)
+
+
+def unignore_logger_for_sentry_logs(
+    name: str,
+) -> None:
+    """Reverts a previous :py:func:`ignore_logger_for_sentry_logs` call,
+    re-enabling recording of Sentry Logs for the named logger.
+
+    :param name: The name of the logger to unignore.
+    """
+    _IGNORED_LOGGERS_SENTRY_LOGS.discard(name)
+
+
 class LoggingIntegration(Integration):
     identifier = "logging"
 
@@ -104,6 +148,7 @@ def _handle_record(self, record: "LogRecord") -> None:
         ):
             self._breadcrumb_handler.handle(record)
 
+    def _handle_sentry_logs_record(self, record: "LogRecord") -> None:
         if (
             self._sentry_logs_handler is not None
             and record.levelno >= self._sentry_logs_handler.level
@@ -118,6 +163,7 @@ def sentry_patched_callhandlers(self: "Any", record: "LogRecord") -> "Any":
             # keeping a local reference because the
             # global might be discarded on shutdown
             ignored_loggers = _IGNORED_LOGGERS
+            ignored_loggers_sentry_logs = _IGNORED_LOGGERS_SENTRY_LOGS
 
             try:
                 return old_callhandlers(self, record)
@@ -126,15 +172,25 @@ def sentry_patched_callhandlers(self: "Any", record: "LogRecord") -> "Any":
                 # the integration.  Otherwise we have a high chance of getting
                 # into a recursion error when the integration is resolved
                 # (this also is slower).
-                if (
-                    ignored_loggers is not None
-                    and record.name.strip() not in ignored_loggers
-                ):
+                name = record.name.strip()
+
+                handle_events = (
+                    ignored_loggers is not None and name not in ignored_loggers
+                )
+                handle_sentry_logs = (
+                    ignored_loggers_sentry_logs is not None
+                    and name not in ignored_loggers_sentry_logs
+                )
+
+                if handle_events or handle_sentry_logs:
                     integration = sentry_sdk.get_client().get_integration(
                         LoggingIntegration
                     )
                     if integration is not None:
-                        integration._handle_record(record)
+                        if handle_events:
+                            integration._handle_record(record)
+                        if handle_sentry_logs:
+                            integration._handle_sentry_logs_record(record)
 
         logging.Logger.callHandlers = sentry_patched_callhandlers  # type: ignore
 
@@ -170,13 +226,6 @@ class _BaseHandler(logging.Handler):
         )
     )
 
-    def _can_record(self, record: "LogRecord") -> bool:
-        """Prevents ignored loggers from recording"""
-        for logger in _IGNORED_LOGGERS:
-            if fnmatch(record.name.strip(), logger):
-                return False
-        return True
-
     def _logging_to_event_level(self, record: "LogRecord") -> str:
         return LOGGING_TO_EVENT_LEVEL.get(
             record.levelno, record.levelname.lower() if record.levelname else ""
@@ -198,6 +247,13 @@ class EventHandler(_BaseHandler):
     Note that you do not have to use this class if the logging integration is enabled, which it is by default.
     """
 
+    def _can_record(self, record: "LogRecord") -> bool:
+        """Prevents ignored loggers from recording"""
+        for logger in _IGNORED_LOGGERS:
+            if fnmatch(record.name.strip(), logger):
+                return False
+        return True
+
     def emit(self, record: "LogRecord") -> "Any":
         with capture_internal_exceptions():
             self.format(record)
@@ -290,6 +346,13 @@ class BreadcrumbHandler(_BaseHandler):
     Note that you do not have to use this class if the logging integration is enabled, which it is by default.
     """
 
+    def _can_record(self, record: "LogRecord") -> bool:
+        """Prevents ignored loggers from recording"""
+        for logger in _IGNORED_LOGGERS:
+            if fnmatch(record.name.strip(), logger):
+                return False
+        return True
+
     def emit(self, record: "LogRecord") -> "Any":
         with capture_internal_exceptions():
             self.format(record)
@@ -321,6 +384,13 @@ class SentryLogsHandler(_BaseHandler):
     Note that you do not have to use this class if the logging integration is enabled, which it is by default.
     """
 
+    def _can_record(self, record: "LogRecord") -> bool:
+        """Prevents ignored loggers from recording"""
+        for logger in _IGNORED_LOGGERS_SENTRY_LOGS:
+            if fnmatch(record.name.strip(), logger):
+                return False
+        return True
+
     def emit(self, record: "LogRecord") -> "Any":
         with capture_internal_exceptions():
             self.format(record)
diff --git a/sentry_sdk/integrations/openai.py b/sentry_sdk/integrations/openai.py
index b1995a6287..a5556b8776 100644
--- a/sentry_sdk/integrations/openai.py
+++ b/sentry_sdk/integrations/openai.py
@@ -71,7 +71,6 @@
         from openai.types.chat import (
             ChatCompletionMessageParam,
             ChatCompletionChunk,
-            ChatCompletionSystemMessageParam,
         )
 except ImportError:
     raise DidNotEnable("OpenAI not installed")
diff --git a/sentry_sdk/integrations/openai_agents/__init__.py b/sentry_sdk/integrations/openai_agents/__init__.py
index 4d778676ac..1268ef3755 100644
--- a/sentry_sdk/integrations/openai_agents/__init__.py
+++ b/sentry_sdk/integrations/openai_agents/__init__.py
@@ -22,7 +22,6 @@
     # not installed. That's why we're adding the second, more specific import
     # after it, even if we don't use it.
     import agents
-    from agents.run import DEFAULT_AGENT_RUNNER
     from agents.run import AgentRunner
     from agents.version import __version__ as OPENAI_AGENTS_VERSION
 
diff --git a/sentry_sdk/integrations/openai_agents/patches/__init__.py b/sentry_sdk/integrations/openai_agents/patches/__init__.py
index e3be2776b3..9ab9e7fab6 100644
--- a/sentry_sdk/integrations/openai_agents/patches/__init__.py
+++ b/sentry_sdk/integrations/openai_agents/patches/__init__.py
@@ -2,9 +2,9 @@
 from .tools import _get_all_tools  # noqa: F401
 from .runner import _create_run_wrapper, _create_run_streamed_wrapper  # noqa: F401
 from .agent_run import (
-    _run_single_turn,
-    _run_single_turn_streamed,
-    _execute_handoffs,
-    _execute_final_output,
-)  # noqa: F401
+    _run_single_turn,  # noqa: F401
+    _run_single_turn_streamed,  # noqa: F401
+    _execute_handoffs,  # noqa: F401
+    _execute_final_output,  # noqa: F401
+)
 from .error_tracing import _patch_error_tracing  # noqa: F401
diff --git a/sentry_sdk/integrations/openai_agents/patches/agent_run.py b/sentry_sdk/integrations/openai_agents/patches/agent_run.py
index a828532ab3..040b10b668 100644
--- a/sentry_sdk/integrations/openai_agents/patches/agent_run.py
+++ b/sentry_sdk/integrations/openai_agents/patches/agent_run.py
@@ -1,5 +1,4 @@
 import sys
-from functools import wraps
 
 from sentry_sdk.consts import SPANDATA
 from sentry_sdk.integrations import DidNotEnable
diff --git a/sentry_sdk/integrations/openai_agents/patches/error_tracing.py b/sentry_sdk/integrations/openai_agents/patches/error_tracing.py
index 8598d9c4fd..9d6fd59e0f 100644
--- a/sentry_sdk/integrations/openai_agents/patches/error_tracing.py
+++ b/sentry_sdk/integrations/openai_agents/patches/error_tracing.py
@@ -1,14 +1,12 @@
 from functools import wraps
 
 import sentry_sdk
-from sentry_sdk.consts import SPANSTATUS
-from sentry_sdk.tracing_utils import set_span_errored
 from ..utils import _record_exception_on_span
 
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
-    from typing import Any, Callable, Optional
+    from typing import Any
 
 
 def _patch_error_tracing() -> None:
diff --git a/sentry_sdk/integrations/openai_agents/spans/__init__.py b/sentry_sdk/integrations/openai_agents/spans/__init__.py
index 64b979fc25..2187c4ee51 100644
--- a/sentry_sdk/integrations/openai_agents/spans/__init__.py
+++ b/sentry_sdk/integrations/openai_agents/spans/__init__.py
@@ -3,7 +3,7 @@
 from .execute_tool import execute_tool_span, update_execute_tool_span  # noqa: F401
 from .handoff import handoff_span  # noqa: F401
 from .invoke_agent import (
-    invoke_agent_span,
-    update_invoke_agent_span,
-    end_invoke_agent_span,
-)  # noqa: F401
+    invoke_agent_span,  # noqa: F401
+    update_invoke_agent_span,  # noqa: F401
+    end_invoke_agent_span,  # noqa: F401
+)
diff --git a/sentry_sdk/integrations/openai_agents/utils.py b/sentry_sdk/integrations/openai_agents/utils.py
index 15119a393c..e496ed7fb5 100644
--- a/sentry_sdk/integrations/openai_agents/utils.py
+++ b/sentry_sdk/integrations/openai_agents/utils.py
@@ -11,6 +11,7 @@
 from sentry_sdk.consts import SPANDATA, SPANSTATUS, OP
 from sentry_sdk.integrations import DidNotEnable
 from sentry_sdk.scope import should_send_default_pii
+from sentry_sdk.tracing import Span
 from sentry_sdk.tracing_utils import set_span_errored
 from sentry_sdk.utils import event_from_exception, safe_serialize
 from sentry_sdk.ai._openai_completions_api import _transform_system_instructions
@@ -22,10 +23,10 @@
 from typing import TYPE_CHECKING
 
 if TYPE_CHECKING:
-    from typing import Any
+    from typing import Any, Union
     from agents import Usage, TResponseInputItem
 
-    from sentry_sdk.tracing import Span
+    from sentry_sdk.traces import StreamedSpan
     from sentry_sdk._types import TextPart
 
 try:
@@ -46,8 +47,15 @@ def _capture_exception(exc: "Any") -> None:
     sentry_sdk.capture_event(event, hint=hint)
 
 
-def _record_exception_on_span(span: "Span", error: Exception) -> "Any":
+def _record_exception_on_span(
+    span: "Union[Span, StreamedSpan]", error: Exception
+) -> "Any":
     set_span_errored(span)
+
+    if not isinstance(span, Span):
+        # TODO[span-first]: make this work with streamedspans
+        return
+
     span.set_data("span.status", "error")
 
     # Optionally capture the error details if we have them
diff --git a/sentry_sdk/integrations/pydantic_ai/__init__.py b/sentry_sdk/integrations/pydantic_ai/__init__.py
index 2f1808d14f..0f0de53fa5 100644
--- a/sentry_sdk/integrations/pydantic_ai/__init__.py
+++ b/sentry_sdk/integrations/pydantic_ai/__init__.py
@@ -2,7 +2,7 @@
 
 
 try:
-    import pydantic_ai  # type: ignore
+    import pydantic_ai  # type: ignore # noqa: F401
 except ImportError:
     raise DidNotEnable("pydantic-ai not installed")
 
diff --git a/sentry_sdk/integrations/pydantic_ai/patches/graph_nodes.py b/sentry_sdk/integrations/pydantic_ai/patches/graph_nodes.py
index 56e46d869f..afb10395f4 100644
--- a/sentry_sdk/integrations/pydantic_ai/patches/graph_nodes.py
+++ b/sentry_sdk/integrations/pydantic_ai/patches/graph_nodes.py
@@ -1,7 +1,6 @@
 from contextlib import asynccontextmanager
 from functools import wraps
 
-import sentry_sdk
 from sentry_sdk.integrations import DidNotEnable
 
 from ..spans import (
diff --git a/sentry_sdk/integrations/pydantic_ai/spans/ai_client.py b/sentry_sdk/integrations/pydantic_ai/spans/ai_client.py
index 8e0b6b9f35..dc95acad45 100644
--- a/sentry_sdk/integrations/pydantic_ai/spans/ai_client.py
+++ b/sentry_sdk/integrations/pydantic_ai/spans/ai_client.py
@@ -29,7 +29,6 @@
 
 if TYPE_CHECKING:
     from typing import Any, List, Dict
-    from pydantic_ai.usage import RequestUsage  # type: ignore
     from pydantic_ai.messages import ModelMessage, SystemPromptPart  # type: ignore
     from sentry_sdk._types import TextPart as SentryTextPart
 
diff --git a/sentry_sdk/integrations/starlette.py b/sentry_sdk/integrations/starlette.py
index 0b797ebcde..dac9887e2f 100644
--- a/sentry_sdk/integrations/starlette.py
+++ b/sentry_sdk/integrations/starlette.py
@@ -552,7 +552,11 @@ def patch_templates() -> None:
     except ImportError:
         return  # Nothing to do
 
-    from starlette.templating import Jinja2Templates  # type: ignore
+    # https://github.com/Kludex/starlette/commit/96479daca2e4bd8157f68d914fd162aa94eff73a
+    try:
+        from starlette.templating import Jinja2Templates  # type: ignore
+    except ImportError:
+        return
 
     old_jinja2templates_init = Jinja2Templates.__init__
 
diff --git a/sentry_sdk/integrations/strawberry.py b/sentry_sdk/integrations/strawberry.py
index 12676b53eb..a12ee63e2a 100644
--- a/sentry_sdk/integrations/strawberry.py
+++ b/sentry_sdk/integrations/strawberry.py
@@ -13,9 +13,7 @@
     capture_internal_exceptions,
     ensure_integration_enabled,
     event_from_exception,
-    logger,
     package_version,
-    _get_installed_modules,
 )
 
 try:
diff --git a/sentry_sdk/logger.py b/sentry_sdk/logger.py
index 4a90fef70b..ee6184105a 100644
--- a/sentry_sdk/logger.py
+++ b/sentry_sdk/logger.py
@@ -4,10 +4,10 @@
 from typing import Any, TYPE_CHECKING
 
 import sentry_sdk
-from sentry_sdk.utils import format_attribute, safe_repr, capture_internal_exceptions
+from sentry_sdk.utils import format_attribute, capture_internal_exceptions
 
 if TYPE_CHECKING:
-    from sentry_sdk._types import Attributes, Log
+    from sentry_sdk._types import Attributes
 
 
 OTEL_RANGES = [
diff --git a/sentry_sdk/metrics.py b/sentry_sdk/metrics.py
index 167e49da05..fb5f21ec4e 100644
--- a/sentry_sdk/metrics.py
+++ b/sentry_sdk/metrics.py
@@ -1,8 +1,8 @@
 import time
-from typing import Any, Optional, TYPE_CHECKING, Union
+from typing import Any, Optional, TYPE_CHECKING
 
 import sentry_sdk
-from sentry_sdk.utils import format_attribute, safe_repr
+from sentry_sdk.utils import format_attribute
 
 if TYPE_CHECKING:
     from sentry_sdk._types import Attributes, Metric, MetricType
diff --git a/sentry_sdk/profiler/continuous_profiler.py b/sentry_sdk/profiler/continuous_profiler.py
index a4c16a63d5..aeeae3fb1d 100644
--- a/sentry_sdk/profiler/continuous_profiler.py
+++ b/sentry_sdk/profiler/continuous_profiler.py
@@ -308,7 +308,7 @@ def reset_buffer(self) -> None:
 
     @property
     def profiler_id(self) -> "Union[str, None]":
-        if self.buffer is None:
+        if not self.running or self.buffer is None:
             return None
         return self.buffer.profiler_id
 
@@ -436,9 +436,9 @@ def run(self) -> None:
             # timestamp so we can use it next iteration
             last = time.perf_counter()
 
-        if self.buffer is not None:
-            self.buffer.flush()
-            self.buffer = None
+        buffer = self.buffer
+        if buffer is not None:
+            buffer.flush()
 
 
 class ThreadContinuousScheduler(ContinuousScheduler):
diff --git a/sentry_sdk/scope.py b/sentry_sdk/scope.py
index a3477cb200..e92c0bf7fc 100644
--- a/sentry_sdk/scope.py
+++ b/sentry_sdk/scope.py
@@ -32,7 +32,6 @@
     has_span_streaming_enabled,
     is_ignored_span,
     _make_sampling_decision,
-    normalize_incoming_data,
     PropagationContext,
 )
 from sentry_sdk.traces import _DEFAULT_PARENT_SPAN, StreamedSpan, NoOpStreamedSpan
@@ -57,7 +56,6 @@
     has_metrics_enabled,
 )
 
-import typing
 from typing import TYPE_CHECKING, cast
 
 if TYPE_CHECKING:
@@ -583,8 +581,12 @@ def get_traceparent(self, *args: "Any", **kwargs: "Any") -> "Optional[str]":
         client = self.get_client()
 
         # If we have an active span, return traceparent from there
-        if has_tracing_enabled(client.options) and self.span is not None:
-            return self.span.to_traceparent()
+        if (
+            has_tracing_enabled(client.options)
+            and self.span is not None
+            and not isinstance(self.span, NoOpStreamedSpan)
+        ):
+            return self.span._to_traceparent()
 
         # else return traceparent from the propagation context
         return self.get_active_propagation_context().to_traceparent()
@@ -597,8 +599,12 @@ def get_baggage(self, *args: "Any", **kwargs: "Any") -> "Optional[Baggage]":
         client = self.get_client()
 
         # If we have an active span, return baggage from there
-        if has_tracing_enabled(client.options) and self.span is not None:
-            return self.span.to_baggage()
+        if (
+            has_tracing_enabled(client.options)
+            and self.span is not None
+            and not isinstance(self.span, NoOpStreamedSpan)
+        ):
+            return self.span._to_baggage()
 
         # else return baggage from the propagation context
         return self.get_active_propagation_context().get_baggage()
@@ -607,8 +613,12 @@ def get_trace_context(self) -> "Dict[str, Any]":
         """
         Returns the Sentry "trace" context from the Propagation Context.
         """
-        if has_tracing_enabled(self.get_client().options) and self._span is not None:
-            return self._span.get_trace_context()
+        if (
+            has_tracing_enabled(self.get_client().options)
+            and self._span is not None
+            and not isinstance(self._span, NoOpStreamedSpan)
+        ):
+            return self._span._get_trace_context()
 
         # if we are tracing externally (otel), those values take precedence
         external_propagation_context = get_external_propagation_context()
@@ -672,8 +682,12 @@ def iter_trace_propagation_headers(
         span = kwargs.pop("span", None)
         span = span or self.span
 
-        if has_tracing_enabled(client.options) and span is not None:
-            for header in span.iter_headers():
+        if (
+            has_tracing_enabled(client.options)
+            and span is not None
+            and not isinstance(span, NoOpStreamedSpan)
+        ):
+            for header in span._iter_headers():
                 yield header
         elif has_external_propagation_context():
             # when we have an external_propagation_context (otlp)
@@ -720,7 +734,7 @@ def clear(self) -> None:
         self.clear_breadcrumbs()
         self._should_capture: bool = True
 
-        self._span: "Optional[Span]" = None
+        self._span: "Optional[Union[Span, StreamedSpan]]" = None
         self._session: "Optional[Session]" = None
         self._force_auto_session_tracking: "Optional[bool]" = None
 
@@ -774,6 +788,14 @@ def transaction(self) -> "Any":
         if self._span is None:
             return None
 
+        if isinstance(self._span, StreamedSpan):
+            warnings.warn(
+                "Scope.transaction is not available in streaming mode.",
+                DeprecationWarning,
+                stacklevel=2,
+            )
+            return None
+
         # there is an orphan span on the scope
         if self._span.containing_transaction is None:
             return None
@@ -803,17 +825,36 @@ def transaction(self, value: "Any") -> None:
             "Assigning to scope.transaction directly is deprecated: use scope.set_transaction_name() instead."
         )
         self._transaction = value
-        if self._span and self._span.containing_transaction:
-            self._span.containing_transaction.name = value
+        if self._span:
+            if isinstance(self._span, StreamedSpan):
+                warnings.warn(
+                    "Scope.transaction is not available in streaming mode.",
+                    DeprecationWarning,
+                    stacklevel=2,
+                )
+                return None
+
+            if self._span.containing_transaction:
+                self._span.containing_transaction.name = value
 
     def set_transaction_name(self, name: str, source: "Optional[str]" = None) -> None:
         """Set the transaction name and optionally the transaction source."""
         self._transaction = name
-
-        if self._span and self._span.containing_transaction:
-            self._span.containing_transaction.name = name
-            if source:
-                self._span.containing_transaction.source = source
+        if self._span:
+            if isinstance(self._span, NoOpStreamedSpan):
+                return
+
+            elif isinstance(self._span, StreamedSpan):
+                self._span._segment.name = name
+                if source:
+                    self._span._segment.set_attribute(
+                        "sentry.span.source", getattr(source, "value", source)
+                    )
+
+            elif self._span.containing_transaction:
+                self._span.containing_transaction.name = name
+                if source:
+                    self._span.containing_transaction.source = source
 
         if source:
             self._transaction_info["source"] = source
@@ -836,12 +877,12 @@ def set_user(self, value: "Optional[Dict[str, Any]]") -> None:
             session.update(user=value)
 
     @property
-    def span(self) -> "Optional[Span]":
+    def span(self) -> "Optional[Union[Span, StreamedSpan]]":
         """Get/set current tracing span or transaction."""
         return self._span
 
     @span.setter
-    def span(self, span: "Optional[Span]") -> None:
+    def span(self, span: "Optional[Union[Span, StreamedSpan]]") -> None:
         self._span = span
         # XXX: this differs from the implementation in JS, there Scope.setSpan
         # does not set Scope._transactionName.
@@ -1150,6 +1191,15 @@ def start_span(
         be removed in the next major version. Going forward, it should only
         be used by the SDK itself.
         """
+        client = sentry_sdk.get_client()
+        if has_span_streaming_enabled(client.options):
+            warnings.warn(
+                "Scope.start_span is not available in streaming mode.",
+                DeprecationWarning,
+                stacklevel=2,
+            )
+            return NoOpSpan()
+
         if kwargs.get("description") is not None:
             warnings.warn(
                 "The `description` parameter is deprecated. Please use `name` instead.",
@@ -1169,6 +1219,9 @@ def start_span(
 
             # get current span or transaction
             span = self.span or self.get_isolation_scope().span
+            if isinstance(span, StreamedSpan):
+                # make mypy happy
+                return NoOpSpan()
 
             if span is None:
                 # New spans get the `trace_id` from the scope
diff --git a/sentry_sdk/traces.py b/sentry_sdk/traces.py
index adf77a4ca8..944e17e5d7 100644
--- a/sentry_sdk/traces.py
+++ b/sentry_sdk/traces.py
@@ -15,6 +15,11 @@
 
 import sentry_sdk
 from sentry_sdk.consts import SPANDATA
+from sentry_sdk.profiler.continuous_profiler import (
+    get_profiler_id,
+    try_autostart_continuous_profiler,
+    try_profile_lifecycle_trace_start,
+)
 from sentry_sdk.tracing_utils import Baggage
 from sentry_sdk.utils import (
     capture_internal_exceptions,
@@ -26,13 +31,18 @@
 )
 
 if TYPE_CHECKING:
-    from typing import Any, Callable, Optional, ParamSpec, TypeVar, Union
+    from typing import Any, Callable, Iterator, Optional, ParamSpec, TypeVar, Union
     from sentry_sdk._types import Attributes, AttributeValue
+    from sentry_sdk.profiler.continuous_profiler import ContinuousProfile
 
     P = ParamSpec("P")
     R = TypeVar("R")
 
 
+BAGGAGE_HEADER_NAME = "baggage"
+SENTRY_TRACE_HEADER_NAME = "sentry-trace"
+
+
 class SpanStatus(str, Enum):
     OK = "ok"
     ERROR = "error"
@@ -228,6 +238,7 @@ class StreamedSpan:
         "_baggage",
         "_sample_rand",
         "_sample_rate",
+        "_continuous_profile",
     )
 
     def __init__(
@@ -280,6 +291,10 @@ def __init__(
 
         self._update_active_thread()
 
+        self._continuous_profile: "Optional[ContinuousProfile]" = None
+        self._start_profile()
+        self._set_profile_id(get_profiler_id())
+
         self._start()
 
     def __repr__(self) -> str:
@@ -328,7 +343,7 @@ def finish(self, end_timestamp: "Optional[Union[float, datetime]]" = None) -> No
     def _start(self) -> None:
         if self._active:
             old_span = self._scope.span
-            self._scope.span = self  # type: ignore
+            self._scope.span = self
             self._previous_span_on_scope = old_span
 
     def _end(self, end_timestamp: "Optional[Union[float, datetime]]" = None) -> None:
@@ -336,6 +351,11 @@ def _end(self, end_timestamp: "Optional[Union[float, datetime]]" = None) -> None
             # This span is already finished, ignore.
             return
 
+        # Stop the profiler
+        if self._is_segment() and self._continuous_profile is not None:
+            with capture_internal_exceptions():
+                self._continuous_profile.stop()
+
         # Detach from scope
         if self._active:
             with capture_internal_exceptions():
@@ -463,6 +483,79 @@ def _update_active_thread(self) -> None:
             if thread_name is not None:
                 self.set_attribute(SPANDATA.THREAD_NAME, thread_name)
 
+    def _dynamic_sampling_context(self) -> "dict[str, str]":
+        return self._segment._get_baggage().dynamic_sampling_context()
+
+    def _to_traceparent(self) -> str:
+        if self.sampled is True:
+            sampled = "1"
+        elif self.sampled is False:
+            sampled = "0"
+        else:
+            sampled = None
+
+        traceparent = "%s-%s" % (self.trace_id, self.span_id)
+        if sampled is not None:
+            traceparent += "-%s" % (sampled,)
+
+        return traceparent
+
+    def _to_baggage(self) -> "Optional[Baggage]":
+        if self._segment:
+            return self._segment._get_baggage()
+        return None
+
+    def _get_baggage(self) -> "Baggage":
+        """
+        Return the :py:class:`~sentry_sdk.tracing_utils.Baggage` associated with
+        the segment.
+
+        The first time a new baggage with Sentry items is made, it will be frozen.
+        """
+        if not self._baggage or self._baggage.mutable:
+            self._baggage = Baggage.populate_from_segment(self)
+
+        return self._baggage
+
+    def _iter_headers(self) -> "Iterator[tuple[str, str]]":
+        if not self._segment:
+            return
+
+        yield SENTRY_TRACE_HEADER_NAME, self._to_traceparent()
+
+        baggage = self._segment._get_baggage().serialize()
+        if baggage:
+            yield BAGGAGE_HEADER_NAME, baggage
+
+    def _get_trace_context(self) -> "dict[str, Any]":
+        # Even if spans themselves are not event-based anymore, we need this
+        # to populate trace context on events
+        context: "dict[str, Any]" = {
+            "trace_id": self.trace_id,
+            "span_id": self.span_id,
+            "parent_span_id": self._parent_span_id,
+            "dynamic_sampling_context": self._dynamic_sampling_context(),
+        }
+
+        if "sentry.op" in self._attributes:
+            context["op"] = self._attributes["sentry.op"]
+        if "sentry.origin" in self._attributes:
+            context["origin"] = self._attributes["sentry.origin"]
+
+        return context
+
+    def _set_profile_id(self, profiler_id: "Optional[str]") -> None:
+        if profiler_id is not None:
+            self.set_attribute("sentry.profiler_id", profiler_id)
+
+    def _start_profile(self) -> None:
+        if not self._is_segment():
+            return
+
+        try_autostart_continuous_profiler()
+
+        self._continuous_profile = try_profile_lifecycle_trace_start()
+
 
 class NoOpStreamedSpan(StreamedSpan):
     __slots__ = (
@@ -498,7 +591,7 @@ def _start(self) -> None:
             return
 
         old_span = self._scope.span
-        self._scope.span = self  # type: ignore
+        self._scope.span = self
         self._previous_span_on_scope = old_span
 
     def _end(self, end_timestamp: "Optional[Union[float, datetime]]" = None) -> None:
diff --git a/sentry_sdk/tracing.py b/sentry_sdk/tracing.py
index a778da7361..7f2baba0c9 100644
--- a/sentry_sdk/tracing.py
+++ b/sentry_sdk/tracing.py
@@ -25,7 +25,6 @@
         List,
         Optional,
         ParamSpec,
-        Set,
         Tuple,
         TypeVar,
         Union,
@@ -771,6 +770,12 @@ def update_active_thread(self) -> None:
         thread_id, thread_name = get_current_thread_meta()
         self.set_thread(thread_id, thread_name)
 
+    # Private aliases matching StreamedSpan's private API
+    _to_traceparent = to_traceparent
+    _to_baggage = to_baggage
+    _iter_headers = iter_headers
+    _get_trace_context = get_trace_context
+
 
 class Transaction(Span):
     """The Transaction is the root element that holds all the spans
@@ -1243,6 +1248,10 @@ def _set_initial_sampling_decision(
                 )
             )
 
+    # Private aliases matching StreamedSpan's private API
+    _get_baggage = get_baggage
+    _get_trace_context = get_trace_context
+
 
 class NoOpSpan(Span):
     def __repr__(self) -> str:
@@ -1324,6 +1333,13 @@ def _set_initial_sampling_decision(
     ) -> None:
         pass
 
+    # Private aliases matching StreamedSpan's private API
+    _to_traceparent = to_traceparent
+    _to_baggage = to_baggage
+    _get_baggage = get_baggage
+    _iter_headers = iter_headers
+    _get_trace_context = get_trace_context
+
 
 if TYPE_CHECKING:
 
diff --git a/sentry_sdk/tracing_utils.py b/sentry_sdk/tracing_utils.py
index d8d1d3d712..9efb01000c 100644
--- a/sentry_sdk/tracing_utils.py
+++ b/sentry_sdk/tracing_utils.py
@@ -767,6 +767,55 @@ def populate_from_transaction(
 
         return Baggage(sentry_items, mutable=False)
 
+    @classmethod
+    def populate_from_segment(cls, segment: "StreamedSpan") -> "Baggage":
+        """
+        Populate fresh baggage entry with sentry_items and make it immutable
+        if this is the head SDK which originates traces.
+        """
+        client = sentry_sdk.get_client()
+        sentry_items: "Dict[str, str]" = {}
+
+        if not client.is_active():
+            return Baggage(sentry_items)
+
+        options = client.options or {}
+
+        sentry_items["trace_id"] = segment.trace_id
+        sentry_items["sample_rand"] = f"{segment._sample_rand:.6f}"  # noqa: E231
+
+        if options.get("environment"):
+            sentry_items["environment"] = options["environment"]
+
+        if options.get("release"):
+            sentry_items["release"] = options["release"]
+
+        if client.parsed_dsn:
+            sentry_items["public_key"] = client.parsed_dsn.public_key
+            if client.parsed_dsn.org_id:
+                sentry_items["org_id"] = client.parsed_dsn.org_id
+
+        if (
+            segment.get_attributes().get("sentry.span.source")
+            not in LOW_QUALITY_SEGMENT_SOURCES
+        ) and segment._name:
+            sentry_items["transaction"] = segment._name
+
+        if segment._sample_rate is not None:
+            sentry_items["sample_rate"] = str(segment._sample_rate)
+
+        if segment.sampled is not None:
+            sentry_items["sampled"] = "true" if segment.sampled else "false"
+
+        # There's an existing baggage but it was mutable, which is why we are
+        # creating this new baggage.
+        # However, if by chance the user put some sentry items in there, give
+        # them precedence.
+        if segment._baggage and segment._baggage.sentry_items:
+            sentry_items.update(segment._baggage.sentry_items)
+
+        return Baggage(sentry_items, mutable=False)
+
     def freeze(self) -> None:
         self.mutable = False
 
@@ -890,6 +939,14 @@ async def async_wrapper(*args: "Any", **kwargs: "Any") -> "Any":
                 )
                 return await f(*args, **kwargs)
 
+            if isinstance(current_span, StreamedSpan):
+                warnings.warn(
+                    "Use the @sentry_sdk.traces.trace decorator in span streaming mode.",
+                    DeprecationWarning,
+                    stacklevel=2,
+                )
+                return await f(*args, **kwargs)
+
             span_op = op or _get_span_op(template)
             function_name = name or qualname_from_function(f) or ""
             span_name = _get_span_name(template, function_name, kwargs)
@@ -927,6 +984,14 @@ def sync_wrapper(*args: "Any", **kwargs: "Any") -> "Any":
                 )
                 return f(*args, **kwargs)
 
+            if isinstance(current_span, StreamedSpan):
+                warnings.warn(
+                    "Use the @sentry_sdk.traces.trace decorator in span streaming mode.",
+                    DeprecationWarning,
+                    stacklevel=2,
+                )
+                return f(*args, **kwargs)
+
             span_op = op or _get_span_op(template)
             function_name = name or qualname_from_function(f) or ""
             span_name = _get_span_name(template, function_name, kwargs)
@@ -1027,7 +1092,9 @@ def sync_wrapper(*args: "Any", **kwargs: "Any") -> "Any":
     return span_decorator
 
 
-def get_current_span(scope: "Optional[sentry_sdk.Scope]" = None) -> "Optional[Span]":
+def get_current_span(
+    scope: "Optional[sentry_sdk.Scope]" = None,
+) -> "Optional[Union[Span, StreamedSpan]]":
     """
     Returns the currently active span if there is one running, otherwise `None`
     """
@@ -1036,16 +1103,24 @@ def get_current_span(scope: "Optional[sentry_sdk.Scope]" = None) -> "Optional[Sp
     return current_span
 
 
-def set_span_errored(span: "Optional[Span]" = None) -> None:
+def set_span_errored(span: "Optional[Union[Span, StreamedSpan]]" = None) -> None:
     """
     Set the status of the current or given span to INTERNAL_ERROR.
     Also sets the status of the transaction (root span) to INTERNAL_ERROR.
     """
+    from sentry_sdk.traces import StreamedSpan, SpanStatus
+
     span = span or get_current_span()
+
     if span is not None:
-        span.set_status(SPANSTATUS.INTERNAL_ERROR)
-        if span.containing_transaction is not None:
-            span.containing_transaction.set_status(SPANSTATUS.INTERNAL_ERROR)
+        if isinstance(span, Span):
+            span.set_status(SPANSTATUS.INTERNAL_ERROR)
+            if span.containing_transaction is not None:
+                span.containing_transaction.set_status(SPANSTATUS.INTERNAL_ERROR)
+        elif isinstance(span, StreamedSpan):
+            span.status = SpanStatus.ERROR
+            if span._segment is not None:
+                span._segment.status = SpanStatus.ERROR
 
 
 def _generate_sample_rand(
@@ -1534,8 +1609,11 @@ def _matches(rule: "Any", value: "Any") -> bool:
     BAGGAGE_HEADER_NAME,
     LOW_QUALITY_TRANSACTION_SOURCES,
     SENTRY_TRACE_HEADER_NAME,
+    Span,
 )
 from sentry_sdk.traces import (
+    LOW_QUALITY_SEGMENT_SOURCES,
+    StreamedSpan,
     start_span as start_streaming_span,
 )
 
diff --git a/sentry_sdk/utils.py b/sentry_sdk/utils.py
index a333467ae9..4dfd36d17c 100644
--- a/sentry_sdk/utils.py
+++ b/sentry_sdk/utils.py
@@ -46,7 +46,6 @@
         Dict,
         Iterator,
         List,
-        Literal,
         NoReturn,
         Optional,
         ParamSpec,
diff --git a/setup.py b/setup.py
index eb8ee4bd4a..299e2f6480 100644
--- a/setup.py
+++ b/setup.py
@@ -21,7 +21,7 @@ def get_file_text(file_name):
 
 setup(
     name="sentry-sdk",
-    version="2.54.0",
+    version="2.56.0",
     author="Sentry Team and Contributors",
     author_email="hello@sentry.io",
     url="https://github.com/getsentry/sentry-python",
diff --git a/tests/conftest.py b/tests/conftest.py
index 0853013dfd..71f2431aac 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -48,6 +48,12 @@
 from sentry_sdk.transport import Transport
 from sentry_sdk.utils import reraise
 
+try:
+    import openai
+except ImportError:
+    openai = None
+
+
 from tests import _warning_recorder, _warning_recorder_mgr
 
 from typing import TYPE_CHECKING
@@ -57,13 +63,6 @@
     from collections.abc import Iterator
 
 try:
-    from anyio import create_memory_object_stream, create_task_group, EndOfStream
-    from mcp.types import (
-        JSONRPCMessage,
-        JSONRPCNotification,
-        JSONRPCRequest,
-    )
-    from mcp.shared.message import SessionMessage
     from httpx import (
         ASGITransport,
         Request as HttpxRequest,
@@ -71,6 +70,22 @@
         AsyncByteStream,
         AsyncClient,
     )
+except ImportError:
+    ASGITransport = None
+    HttpxRequest = None
+    HttpxResponse = None
+    AsyncByteStream = None
+    AsyncClient = None
+
+
+try:
+    from anyio import create_memory_object_stream, create_task_group, EndOfStream
+    from mcp.types import (
+        JSONRPCMessage,
+        JSONRPCNotification,
+        JSONRPCRequest,
+    )
+    from mcp.shared.message import SessionMessage
 except ImportError:
     create_memory_object_stream = None
     create_task_group = None
@@ -81,12 +96,6 @@
     JSONRPCRequest = None
     SessionMessage = None
 
-    ASGITransport = None
-    HttpxRequest = None
-    HttpxResponse = None
-    AsyncByteStream = None
-    AsyncClient = None
-
 
 SENTRY_EVENT_SCHEMA = "./checkouts/data-schemas/relay/event.schema.json"
 
@@ -1013,6 +1022,145 @@ async def inner(values):
     return inner
 
 
+@pytest.fixture
+def server_side_event_chunks():
+    def inner(events, include_event_type=True):
+        for event in events:
+            payload = event.model_dump()
+            chunk = (
+                f"event: {payload['type']}\ndata: {json.dumps(payload)}\n\n"
+                if include_event_type
+                else f"data: {json.dumps(payload)}\n\n"
+            )
+            yield chunk.encode("utf-8")
+
+    return inner
+
+
+@pytest.fixture
+def get_model_response():
+    def inner(response_content, serialize_pydantic=False, request_headers=None):
+        if request_headers is None:
+            request_headers = {}
+
+        model_request = HttpxRequest(
+            "POST",
+            "/responses",
+            headers=request_headers,
+        )
+
+        if serialize_pydantic:
+            response_content = json.dumps(response_content.model_dump()).encode("utf-8")
+
+        response = HttpxResponse(
+            200,
+            request=model_request,
+            content=response_content,
+        )
+
+        return response
+
+    return inner
+
+
+@pytest.fixture
+def nonstreaming_responses_model_response():
+    return openai.types.responses.Response(
+        id="resp_123",
+        output=[
+            openai.types.responses.ResponseOutputMessage(
+                id="msg_123",
+                type="message",
+                status="completed",
+                content=[
+                    openai.types.responses.ResponseOutputText(
+                        text="Hello, how can I help you?",
+                        type="output_text",
+                        annotations=[],
+                    )
+                ],
+                role="assistant",
+            )
+        ],
+        parallel_tool_calls=False,
+        tool_choice="none",
+        tools=[],
+        created_at=10000000,
+        model="gpt-4",
+        object="response",
+        usage=openai.types.responses.ResponseUsage(
+            input_tokens=10,
+            input_tokens_details=openai.types.responses.response_usage.InputTokensDetails(
+                cached_tokens=0,
+            ),
+            output_tokens=20,
+            output_tokens_details=openai.types.responses.response_usage.OutputTokensDetails(
+                reasoning_tokens=5,
+            ),
+            total_tokens=30,
+        ),
+    )
+
+
+@pytest.fixture
+def responses_tool_call_model_responses():
+    def inner(
+        tool_name: str,
+        arguments: str,
+        response_model: str,
+        response_text: str,
+        response_ids: "Iterator[str]",
+        usages: "Iterator[openai.types.responses.ResponseUsage]",
+    ):
+        yield openai.types.responses.Response(
+            id=next(response_ids),
+            output=[
+                openai.types.responses.ResponseFunctionToolCall(
+                    id="call_123",
+                    call_id="call_123",
+                    name=tool_name,
+                    type="function_call",
+                    arguments=arguments,
+                )
+            ],
+            parallel_tool_calls=False,
+            tool_choice="none",
+            tools=[],
+            created_at=10000000,
+            model=response_model,
+            object="response",
+            usage=next(usages),
+        )
+
+        yield openai.types.responses.Response(
+            id=next(response_ids),
+            output=[
+                openai.types.responses.ResponseOutputMessage(
+                    id="msg_final",
+                    type="message",
+                    status="completed",
+                    content=[
+                        openai.types.responses.ResponseOutputText(
+                            text=response_text,
+                            type="output_text",
+                            annotations=[],
+                        )
+                    ],
+                    role="assistant",
+                )
+            ],
+            parallel_tool_calls=False,
+            tool_choice="none",
+            tools=[],
+            created_at=10000000,
+            model=response_model,
+            object="response",
+            usage=next(usages),
+        )
+
+    return inner
+
+
 class MockServerRequestHandler(BaseHTTPRequestHandler):
     def do_GET(self):  # noqa: N802
         # Process an HTTP GET request and return a response.
diff --git a/tests/integrations/anthropic/test_anthropic.py b/tests/integrations/anthropic/test_anthropic.py
index ea48f5d4db..bd9a41e701 100644
--- a/tests/integrations/anthropic/test_anthropic.py
+++ b/tests/integrations/anthropic/test_anthropic.py
@@ -11,7 +11,7 @@ async def __call__(self, *args, **kwargs):
             return super(AsyncMock, self).__call__(*args, **kwargs)
 
 
-from anthropic import Anthropic, AnthropicError, AsyncAnthropic, AsyncStream, Stream
+from anthropic import Anthropic, AnthropicError, AsyncAnthropic
 from anthropic.types import MessageDeltaUsage, TextDelta, Usage
 from anthropic.types.content_block_delta_event import ContentBlockDeltaEvent
 from anthropic.types.content_block_start_event import ContentBlockStartEvent
@@ -20,6 +20,14 @@ async def __call__(self, *args, **kwargs):
 from anthropic.types.message_delta_event import MessageDeltaEvent
 from anthropic.types.message_start_event import MessageStartEvent
 
+try:
+    from anthropic.types import ErrorResponse, OverloadedError
+    from anthropic import APIStatusError
+except ImportError:
+    ErrorResponse = None
+    OverloadedError = None
+    APIStatusError = None
+
 try:
     from anthropic.types import InputJSONDelta
 except ImportError:
@@ -28,6 +36,11 @@ async def __call__(self, *args, **kwargs):
     except ImportError:
         pass
 
+try:
+    from anthropic.lib.streaming import TextEvent
+except ImportError:
+    TextEvent = None
+
 try:
     # 0.27+
     from anthropic.types.raw_message_delta_event import Delta
@@ -58,11 +71,12 @@ async def __call__(self, *args, **kwargs):
 ANTHROPIC_VERSION = package_version("anthropic")
 
 EXAMPLE_MESSAGE = Message(
-    id="id",
+    id="msg_01XFDUDYJgAACzvnptvVoYEL",
     model="model",
     role="assistant",
     content=[TextBlock(type="text", text="Hi, I'm Claude.")],
     type="message",
+    stop_reason="end_turn",
     usage=Usage(input_tokens=10, output_tokens=20),
 )
 
@@ -117,6 +131,80 @@ def test_nonstreaming_create_message(
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    if send_default_pii and include_prompts:
+        assert (
+            span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+            == '[{"role": "user", "content": "Hello, Claude"}]'
+        )
+        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi, I'm Claude."
+    else:
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is False
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS] == ["end_turn"]
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+async def test_nonstreaming_create_message_async(
+    sentry_init, capture_events, send_default_pii, include_prompts
+):
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=include_prompts)],
+        traces_sample_rate=1.0,
+        send_default_pii=send_default_pii,
+    )
+    events = capture_events()
+    client = AsyncAnthropic(api_key="z")
+    client.messages._post = AsyncMock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        response = await client.messages.create(
+            max_tokens=1024, messages=messages, model="model"
+        )
+
+    assert response == EXAMPLE_MESSAGE
+    usage = response.usage
+
+    assert usage.input_tokens == 10
+    assert usage.output_tokens == 20
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    assert len(event["spans"]) == 1
+    (span,) = event["spans"]
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
@@ -134,29 +222,1269 @@ def test_nonstreaming_create_message(
     assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
     assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
     assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is False
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+
+
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+def test_streaming_create_message(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    server_side_event_chunks,
+):
+    client = Anthropic(api_key="z")
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=EXAMPLE_MESSAGE,
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=TextBlock(type="text", text=""),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="Hi", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockStopEvent(type="content_block_stop", index=0),
+                MessageDeltaEvent(
+                    delta=Delta(stop_reason="max_tokens"),
+                    usage=MessageDeltaUsage(output_tokens=10),
+                    type="message_delta",
+                ),
+            ]
+        )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=include_prompts)],
+        traces_sample_rate=1.0,
+        send_default_pii=send_default_pii,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            message = client.messages.create(
+                max_tokens=1024, messages=messages, model="model", stream=True
+            )
+
+            for _ in message:
+                pass
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    if send_default_pii and include_prompts:
+        assert (
+            span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+            == '[{"role": "user", "content": "Hello, Claude"}]'
+        )
+        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
+
+    else:
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS] == ["max_tokens"]
+
+
+def test_streaming_create_message_close(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    server_side_event_chunks,
+):
+    client = Anthropic(api_key="z")
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=EXAMPLE_MESSAGE,
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=TextBlock(type="text", text=""),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="Hi", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockStopEvent(type="content_block_stop", index=0),
+                MessageDeltaEvent(
+                    delta=Delta(stop_reason="max_tokens"),
+                    usage=MessageDeltaUsage(output_tokens=10),
+                    type="message_delta",
+                ),
+            ]
+        )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            messages = client.messages.create(
+                max_tokens=1024, messages=messages, model="model", stream=True
+            )
+
+            for _ in range(4):
+                next(messages)
+
+            messages.close()
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    assert (
+        span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+        == '[{"role": "user", "content": "Hello, Claude"}]'
+    )
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi!"
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+
+
+@pytest.mark.skipif(
+    ANTHROPIC_VERSION < (0, 41),
+    reason="Error classes moved in https://github.com/anthropics/anthropic-sdk-python/commit/4e0b15e22fe40e9aa513459564f641bf97c90954.",
+)
+def test_streaming_create_message_api_error(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    server_side_event_chunks,
+):
+    client = Anthropic(api_key="z")
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=EXAMPLE_MESSAGE,
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=TextBlock(type="text", text=""),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="Hi", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ErrorResponse(
+                    type="error",
+                    error=OverloadedError(
+                        message="Overloaded", type="overloaded_error"
+                    ),
+                ),
+            ]
+        )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with pytest.raises(APIStatusError), mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            message = client.messages.create(
+                max_tokens=1024, messages=messages, model="model", stream=True
+            )
+
+            for _ in message:
+                pass
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    assert (
+        span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+        == '[{"role": "user", "content": "Hello, Claude"}]'
+    )
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi!"
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+
+    assert span["status"] == "internal_error"
+    assert span["tags"]["status"] == "internal_error"
+    assert event["contexts"]["trace"]["status"] == "internal_error"
+
+
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+def test_stream_messages(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    server_side_event_chunks,
+):
+    client = Anthropic(api_key="z")
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=EXAMPLE_MESSAGE,
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=TextBlock(type="text", text=""),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="Hi", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockStopEvent(type="content_block_stop", index=0),
+                MessageDeltaEvent(
+                    delta=Delta(stop_reason="max_tokens"),
+                    usage=MessageDeltaUsage(output_tokens=10),
+                    type="message_delta",
+                ),
+            ]
+        )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=include_prompts)],
+        traces_sample_rate=1.0,
+        send_default_pii=send_default_pii,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+            ) as stream:
+                for event in stream:
+                    pass
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    if send_default_pii and include_prompts:
+        assert (
+            span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+            == '[{"role": "user", "content": "Hello, Claude"}]'
+        )
+        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
+
+    else:
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS] == ["max_tokens"]
+
+
+def test_stream_messages_close(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    server_side_event_chunks,
+):
+    client = Anthropic(api_key="z")
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=EXAMPLE_MESSAGE,
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=TextBlock(type="text", text=""),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="Hi", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockStopEvent(type="content_block_stop", index=0),
+                MessageDeltaEvent(
+                    delta=Delta(stop_reason="max_tokens"),
+                    usage=MessageDeltaUsage(output_tokens=10),
+                    type="message_delta",
+                ),
+            ]
+        )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+            ) as stream:
+                for _ in range(4):
+                    next(stream)
+
+                # New versions add TextEvent, so consume one more event.
+                if TextEvent is not None and isinstance(next(stream), TextEvent):
+                    next(stream)
+
+                stream.close()
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    assert (
+        span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+        == '[{"role": "user", "content": "Hello, Claude"}]'
+    )
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi!"
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+
+
+@pytest.mark.skipif(
+    ANTHROPIC_VERSION < (0, 41),
+    reason="Error classes moved in https://github.com/anthropics/anthropic-sdk-python/commit/4e0b15e22fe40e9aa513459564f641bf97c90954.",
+)
+def test_stream_messages_api_error(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    server_side_event_chunks,
+):
+    client = Anthropic(api_key="z")
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=EXAMPLE_MESSAGE,
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=TextBlock(type="text", text=""),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="Hi", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ErrorResponse(
+                    type="error",
+                    error=OverloadedError(
+                        message="Overloaded", type="overloaded_error"
+                    ),
+                ),
+            ]
+        )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with pytest.raises(APIStatusError), mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+            ) as stream:
+                for event in stream:
+                    pass
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    assert (
+        span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+        == '[{"role": "user", "content": "Hello, Claude"}]'
+    )
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi!"
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+
+    assert span["status"] == "internal_error"
+    assert span["tags"]["status"] == "internal_error"
+    assert event["contexts"]["trace"]["status"] == "internal_error"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+async def test_streaming_create_message_async(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
+):
+    client = AsyncAnthropic(api_key="z")
+
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=EXAMPLE_MESSAGE,
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=TextBlock(type="text", text=""),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="Hi", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockStopEvent(type="content_block_stop", index=0),
+                    MessageDeltaEvent(
+                        delta=Delta(stop_reason="max_tokens"),
+                        usage=MessageDeltaUsage(output_tokens=10),
+                        type="message_delta",
+                    ),
+                ]
+            )
+        ),
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=include_prompts)],
+        traces_sample_rate=1.0,
+        default_integrations=False,
+        send_default_pii=send_default_pii,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            message = await client.messages.create(
+                max_tokens=1024, messages=messages, model="model", stream=True
+            )
+
+            async for _ in message:
+                pass
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    assert len(event["spans"]) == 1
+    (span,) = event["spans"]
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    if send_default_pii and include_prompts:
+        assert (
+            span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+            == '[{"role": "user", "content": "Hello, Claude"}]'
+        )
+        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
+
+    else:
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS] == ["max_tokens"]
+
+
+@pytest.mark.asyncio
+async def test_streaming_create_message_async_close(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
+):
+    client = AsyncAnthropic(api_key="z")
+
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=EXAMPLE_MESSAGE,
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=TextBlock(type="text", text=""),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="Hi", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockStopEvent(type="content_block_stop", index=0),
+                    MessageDeltaEvent(
+                        delta=Delta(stop_reason="max_tokens"),
+                        usage=MessageDeltaUsage(output_tokens=10),
+                        type="message_delta",
+                    ),
+                ]
+            )
+        )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            messages = await client.messages.create(
+                max_tokens=1024, messages=messages, model="model", stream=True
+            )
+
+            for _ in range(4):
+                await messages.__anext__()
+            await messages.close()
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    assert (
+        span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+        == '[{"role": "user", "content": "Hello, Claude"}]'
+    )
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi!"
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+
+
+@pytest.mark.skipif(
+    ANTHROPIC_VERSION < (0, 41),
+    reason="Error classes moved in https://github.com/anthropics/anthropic-sdk-python/commit/4e0b15e22fe40e9aa513459564f641bf97c90954.",
+)
+@pytest.mark.asyncio
+async def test_streaming_create_message_async_api_error(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
+):
+    client = AsyncAnthropic(api_key="z")
+
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=EXAMPLE_MESSAGE,
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=TextBlock(type="text", text=""),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="Hi", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ErrorResponse(
+                        type="error",
+                        error=OverloadedError(
+                            message="Overloaded", type="overloaded_error"
+                        ),
+                    ),
+                ]
+            )
+        )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with pytest.raises(APIStatusError), mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            message = await client.messages.create(
+                max_tokens=1024, messages=messages, model="model", stream=True
+            )
+
+            async for _ in message:
+                pass
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    assert (
+        span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+        == '[{"role": "user", "content": "Hello, Claude"}]'
+    )
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi!"
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+
+    assert span["status"] == "internal_error"
+    assert span["tags"]["status"] == "internal_error"
+    assert event["contexts"]["trace"]["status"] == "internal_error"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+async def test_stream_message_async(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
+):
+    client = AsyncAnthropic(api_key="z")
+
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=EXAMPLE_MESSAGE,
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=TextBlock(type="text", text=""),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="Hi", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockStopEvent(type="content_block_stop", index=0),
+                    MessageDeltaEvent(
+                        delta=Delta(),
+                        usage=MessageDeltaUsage(output_tokens=10),
+                        type="message_delta",
+                    ),
+                ]
+            )
+        ),
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=include_prompts)],
+        traces_sample_rate=1.0,
+        send_default_pii=send_default_pii,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            async with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+            ) as stream:
+                async for event in stream:
+                    pass
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    assert len(event["spans"]) == 1
+    (span,) = event["spans"]
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    if send_default_pii and include_prompts:
+        assert (
+            span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+            == '[{"role": "user", "content": "Hello, Claude"}]'
+        )
+        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
+
+    else:
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+
+
+@pytest.mark.skipif(
+    ANTHROPIC_VERSION < (0, 41),
+    reason="Error classes moved in https://github.com/anthropics/anthropic-sdk-python/commit/4e0b15e22fe40e9aa513459564f641bf97c90954.",
+)
+@pytest.mark.asyncio
+async def test_stream_messages_async_api_error(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
+):
+    client = AsyncAnthropic(api_key="z")
+
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=EXAMPLE_MESSAGE,
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=TextBlock(type="text", text=""),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="Hi", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ErrorResponse(
+                        type="error",
+                        error=OverloadedError(
+                            message="Overloaded", type="overloaded_error"
+                        ),
+                    ),
+                ]
+            )
+        )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=True)],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with pytest.raises(APIStatusError), mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            async with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+            ) as stream:
+                async for event in stream:
+                    pass
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    assert (
+        span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+        == '[{"role": "user", "content": "Hello, Claude"}]'
+    )
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi!"
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
+
+    assert span["status"] == "internal_error"
+    assert span["tags"]["status"] == "internal_error"
+    assert event["contexts"]["trace"]["status"] == "internal_error"
 
 
 @pytest.mark.asyncio
-@pytest.mark.parametrize(
-    "send_default_pii, include_prompts",
-    [
-        (True, True),
-        (True, False),
-        (False, True),
-        (False, False),
-    ],
-)
-async def test_nonstreaming_create_message_async(
-    sentry_init, capture_events, send_default_pii, include_prompts
+async def test_stream_messages_async_close(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
 ):
+    client = AsyncAnthropic(api_key="z")
+
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=EXAMPLE_MESSAGE,
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=TextBlock(type="text", text=""),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="Hi", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockStopEvent(type="content_block_stop", index=0),
+                    MessageDeltaEvent(
+                        delta=Delta(stop_reason="max_tokens"),
+                        usage=MessageDeltaUsage(output_tokens=10),
+                        type="message_delta",
+                    ),
+                ]
+            )
+        )
+    )
+
     sentry_init(
-        integrations=[AnthropicIntegration(include_prompts=include_prompts)],
+        integrations=[AnthropicIntegration(include_prompts=True)],
         traces_sample_rate=1.0,
-        send_default_pii=send_default_pii,
+        send_default_pii=True,
     )
     events = capture_events()
-    client = AsyncAnthropic(api_key="z")
-    client.messages._post = AsyncMock(return_value=EXAMPLE_MESSAGE)
 
     messages = [
         {
@@ -165,16 +1493,27 @@ async def test_nonstreaming_create_message_async(
         }
     ]
 
-    with start_transaction(name="anthropic"):
-        response = await client.messages.create(
-            max_tokens=1024, messages=messages, model="model"
-        )
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            async with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+            ) as stream:
+                for _ in range(4):
+                    await stream.__anext__()
 
-    assert response == EXAMPLE_MESSAGE
-    usage = response.usage
+                # New versions add TextEvent, so consume one more event.
+                if TextEvent is not None and isinstance(
+                    await stream.__anext__(), TextEvent
+                ):
+                    await stream.__anext__()
 
-    assert usage.input_tokens == 10
-    assert usage.output_tokens == 20
+                await stream.close()
 
     assert len(events) == 1
     (event,) = events
@@ -182,30 +1521,31 @@ async def test_nonstreaming_create_message_async(
     assert event["type"] == "transaction"
     assert event["transaction"] == "anthropic"
 
-    assert len(event["spans"]) == 1
-    (span,) = event["spans"]
+    span = next(span for span in event["spans"] if span["op"] == OP.GEN_AI_CHAT)
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
-    if send_default_pii and include_prompts:
-        assert (
-            span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-            == '[{"role": "user", "content": "Hello, Claude"}]'
-        )
-        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi, I'm Claude."
-    else:
-        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
-        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+    assert (
+        span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
+        == '[{"role": "user", "content": "Hello, Claude"}]'
+    )
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi!"
 
     assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
     assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
     assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
-    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is False
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_ID] == "msg_01XFDUDYJgAACzvnptvVoYEL"
 
 
+@pytest.mark.skipif(
+    ANTHROPIC_VERSION < (0, 27),
+    reason="Versions <0.27.0 do not include InputJSONDelta, which was introduced in >=0.27.0 along with a new message delta type for tool calling.",
+)
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [
@@ -215,43 +1555,82 @@ async def test_nonstreaming_create_message_async(
         (False, False),
     ],
 )
-def test_streaming_create_message(
-    sentry_init, capture_events, send_default_pii, include_prompts
+def test_streaming_create_message_with_input_json_delta(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    server_side_event_chunks,
 ):
     client = Anthropic(api_key="z")
-    returned_stream = Stream(cast_to=None, response=None, client=client)
-    returned_stream._iterator = [
-        MessageStartEvent(
-            message=EXAMPLE_MESSAGE,
-            type="message_start",
-        ),
-        ContentBlockStartEvent(
-            type="content_block_start",
-            index=0,
-            content_block=TextBlock(type="text", text=""),
-        ),
-        ContentBlockDeltaEvent(
-            delta=TextDelta(text="Hi", type="text_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockDeltaEvent(
-            delta=TextDelta(text="!", type="text_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockDeltaEvent(
-            delta=TextDelta(text=" I'm Claude!", type="text_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockStopEvent(type="content_block_stop", index=0),
-        MessageDeltaEvent(
-            delta=Delta(),
-            usage=MessageDeltaUsage(output_tokens=10),
-            type="message_delta",
-        ),
-    ]
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=Message(
+                        id="msg_0",
+                        content=[],
+                        model="claude-3-5-sonnet-20240620",
+                        role="assistant",
+                        stop_reason=None,
+                        stop_sequence=None,
+                        type="message",
+                        usage=Usage(input_tokens=366, output_tokens=10),
+                    ),
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=ToolUseBlock(
+                        id="toolu_0", input={}, name="get_weather", type="tool_use"
+                    ),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(partial_json="", type="input_json_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(
+                        partial_json='{"location": "', type="input_json_delta"
+                    ),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(partial_json="S", type="input_json_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(partial_json="an ", type="input_json_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(
+                        partial_json="Francisco, C", type="input_json_delta"
+                    ),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(partial_json='A"}', type="input_json_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockStopEvent(type="content_block_stop", index=0),
+                MessageDeltaEvent(
+                    delta=Delta(stop_reason="tool_use", stop_sequence=None),
+                    usage=MessageDeltaUsage(output_tokens=41),
+                    type="message_delta",
+                ),
+            ]
+        )
+    )
 
     sentry_init(
         integrations=[AnthropicIntegration(include_prompts=include_prompts)],
@@ -259,24 +1638,27 @@ def test_streaming_create_message(
         send_default_pii=send_default_pii,
     )
     events = capture_events()
-    client.messages._post = mock.Mock(return_value=returned_stream)
 
     messages = [
         {
             "role": "user",
-            "content": "Hello, Claude",
+            "content": "What is the weather like in San Francisco?",
         }
     ]
 
-    with start_transaction(name="anthropic"):
-        message = client.messages.create(
-            max_tokens=1024, messages=messages, model="model", stream=True
-        )
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            message = client.messages.create(
+                max_tokens=1024, messages=messages, model="model", stream=True
+            )
 
-        for _ in message:
-            pass
+            for _ in message:
+                pass
 
-    assert message == returned_stream
     assert len(events) == 1
     (event,) = events
 
@@ -288,27 +1670,33 @@ def test_streaming_create_message(
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
     if send_default_pii and include_prompts:
         assert (
             span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-            == '[{"role": "user", "content": "Hello, Claude"}]'
+            == '[{"role": "user", "content": "What is the weather like in San Francisco?"}]'
+        )
+        assert (
+            span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
+            == '{"location": "San Francisco, CA"}'
         )
-        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
-
     else:
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
 
-    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
-    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 10
-    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 366
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 41
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 407
     assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
 
 
-@pytest.mark.asyncio
+@pytest.mark.skipif(
+    ANTHROPIC_VERSION < (0, 27),
+    reason="Versions <0.27.0 do not include InputJSONDelta, which was introduced in >=0.27.0 along with a new message delta type for tool calling.",
+)
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [
@@ -318,44 +1706,81 @@ def test_streaming_create_message(
         (False, False),
     ],
 )
-async def test_streaming_create_message_async(
-    sentry_init, capture_events, send_default_pii, include_prompts, async_iterator
+def test_stream_messages_with_input_json_delta(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    server_side_event_chunks,
 ):
-    client = AsyncAnthropic(api_key="z")
-    returned_stream = AsyncStream(cast_to=None, response=None, client=client)
-    returned_stream._iterator = async_iterator(
-        [
-            MessageStartEvent(
-                message=EXAMPLE_MESSAGE,
-                type="message_start",
-            ),
-            ContentBlockStartEvent(
-                type="content_block_start",
-                index=0,
-                content_block=TextBlock(type="text", text=""),
-            ),
-            ContentBlockDeltaEvent(
-                delta=TextDelta(text="Hi", type="text_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockDeltaEvent(
-                delta=TextDelta(text="!", type="text_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockDeltaEvent(
-                delta=TextDelta(text=" I'm Claude!", type="text_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockStopEvent(type="content_block_stop", index=0),
-            MessageDeltaEvent(
-                delta=Delta(),
-                usage=MessageDeltaUsage(output_tokens=10),
-                type="message_delta",
-            ),
-        ]
+    client = Anthropic(api_key="z")
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=Message(
+                        id="msg_0",
+                        content=[],
+                        model="claude-3-5-sonnet-20240620",
+                        role="assistant",
+                        stop_reason=None,
+                        stop_sequence=None,
+                        type="message",
+                        usage=Usage(input_tokens=366, output_tokens=10),
+                    ),
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=ToolUseBlock(
+                        id="toolu_0", input={}, name="get_weather", type="tool_use"
+                    ),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(partial_json="", type="input_json_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(
+                        partial_json='{"location": "', type="input_json_delta"
+                    ),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(partial_json="S", type="input_json_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(partial_json="an ", type="input_json_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(
+                        partial_json="Francisco, C", type="input_json_delta"
+                    ),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=InputJSONDelta(partial_json='A"}', type="input_json_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockStopEvent(type="content_block_stop", index=0),
+                MessageDeltaEvent(
+                    delta=Delta(stop_reason="tool_use", stop_sequence=None),
+                    usage=MessageDeltaUsage(output_tokens=41),
+                    type="message_delta",
+                ),
+            ]
+        )
     )
 
     sentry_init(
@@ -364,24 +1789,28 @@ async def test_streaming_create_message_async(
         send_default_pii=send_default_pii,
     )
     events = capture_events()
-    client.messages._post = AsyncMock(return_value=returned_stream)
 
     messages = [
         {
             "role": "user",
-            "content": "Hello, Claude",
+            "content": "What is the weather like in San Francisco?",
         }
     ]
 
-    with start_transaction(name="anthropic"):
-        message = await client.messages.create(
-            max_tokens=1024, messages=messages, model="model", stream=True
-        )
-
-        async for _ in message:
-            pass
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+            ) as stream:
+                for event in stream:
+                    pass
 
-    assert message == returned_stream
     assert len(events) == 1
     (event,) = events
 
@@ -393,26 +1822,30 @@ async def test_streaming_create_message_async(
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
     if send_default_pii and include_prompts:
         assert (
             span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
-            == '[{"role": "user", "content": "Hello, Claude"}]'
+            == '[{"role": "user", "content": "What is the weather like in San Francisco?"}]'
+        )
+        assert (
+            span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
+            == '{"location": "San Francisco, CA"}'
         )
-        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
-
     else:
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
 
-    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
-    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 10
-    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 366
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 41
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 407
     assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
 
 
+@pytest.mark.asyncio
 @pytest.mark.skipif(
     ANTHROPIC_VERSION < (0, 27),
     reason="Versions <0.27.0 do not include InputJSONDelta, which was introduced in >=0.27.0 along with a new message delta type for tool calling.",
@@ -426,69 +1859,88 @@ async def test_streaming_create_message_async(
         (False, False),
     ],
 )
-def test_streaming_create_message_with_input_json_delta(
-    sentry_init, capture_events, send_default_pii, include_prompts
+async def test_streaming_create_message_with_input_json_delta_async(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
 ):
-    client = Anthropic(api_key="z")
-    returned_stream = Stream(cast_to=None, response=None, client=client)
-    returned_stream._iterator = [
-        MessageStartEvent(
-            message=Message(
-                id="msg_0",
-                content=[],
-                model="claude-3-5-sonnet-20240620",
-                role="assistant",
-                stop_reason=None,
-                stop_sequence=None,
-                type="message",
-                usage=Usage(input_tokens=366, output_tokens=10),
-            ),
-            type="message_start",
-        ),
-        ContentBlockStartEvent(
-            type="content_block_start",
-            index=0,
-            content_block=ToolUseBlock(
-                id="toolu_0", input={}, name="get_weather", type="tool_use"
-            ),
-        ),
-        ContentBlockDeltaEvent(
-            delta=InputJSONDelta(partial_json="", type="input_json_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockDeltaEvent(
-            delta=InputJSONDelta(partial_json="{'location':", type="input_json_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockDeltaEvent(
-            delta=InputJSONDelta(partial_json=" 'S", type="input_json_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockDeltaEvent(
-            delta=InputJSONDelta(partial_json="an ", type="input_json_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockDeltaEvent(
-            delta=InputJSONDelta(partial_json="Francisco, C", type="input_json_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockDeltaEvent(
-            delta=InputJSONDelta(partial_json="A'}", type="input_json_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockStopEvent(type="content_block_stop", index=0),
-        MessageDeltaEvent(
-            delta=Delta(stop_reason="tool_use", stop_sequence=None),
-            usage=MessageDeltaUsage(output_tokens=41),
-            type="message_delta",
-        ),
-    ]
+    client = AsyncAnthropic(api_key="z")
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=Message(
+                            id="msg_0",
+                            content=[],
+                            model="claude-3-5-sonnet-20240620",
+                            role="assistant",
+                            stop_reason=None,
+                            stop_sequence=None,
+                            type="message",
+                            usage=Usage(input_tokens=366, output_tokens=10),
+                        ),
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=ToolUseBlock(
+                            id="toolu_0", input={}, name="get_weather", type="tool_use"
+                        ),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(partial_json="", type="input_json_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(
+                            partial_json='{"location": "', type="input_json_delta"
+                        ),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(partial_json="S", type="input_json_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(
+                            partial_json="an ", type="input_json_delta"
+                        ),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(
+                            partial_json="Francisco, C", type="input_json_delta"
+                        ),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(
+                            partial_json='A"}', type="input_json_delta"
+                        ),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockStopEvent(type="content_block_stop", index=0),
+                    MessageDeltaEvent(
+                        delta=Delta(stop_reason="tool_use", stop_sequence=None),
+                        usage=MessageDeltaUsage(output_tokens=41),
+                        type="message_delta",
+                    ),
+                ]
+            )
+        )
+    )
 
     sentry_init(
         integrations=[AnthropicIntegration(include_prompts=include_prompts)],
@@ -496,7 +1948,6 @@ def test_streaming_create_message_with_input_json_delta(
         send_default_pii=send_default_pii,
     )
     events = capture_events()
-    client.messages._post = mock.Mock(return_value=returned_stream)
 
     messages = [
         {
@@ -505,15 +1956,19 @@ def test_streaming_create_message_with_input_json_delta(
         }
     ]
 
-    with start_transaction(name="anthropic"):
-        message = client.messages.create(
-            max_tokens=1024, messages=messages, model="model", stream=True
-        )
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            message = await client.messages.create(
+                max_tokens=1024, messages=messages, model="model", stream=True
+            )
 
-        for _ in message:
-            pass
+            async for _ in message:
+                pass
 
-    assert message == returned_stream
     assert len(events) == 1
     (event,) = events
 
@@ -525,6 +1980,7 @@ def test_streaming_create_message_with_input_json_delta(
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
@@ -535,8 +1991,9 @@ def test_streaming_create_message_with_input_json_delta(
         )
         assert (
             span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
-            == "{'location': 'San Francisco, CA'}"
+            == '{"location": "San Francisco, CA"}'
         )
+
     else:
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
@@ -561,74 +2018,87 @@ def test_streaming_create_message_with_input_json_delta(
         (False, False),
     ],
 )
-async def test_streaming_create_message_with_input_json_delta_async(
-    sentry_init, capture_events, send_default_pii, include_prompts, async_iterator
+async def test_stream_message_with_input_json_delta_async(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
 ):
     client = AsyncAnthropic(api_key="z")
-    returned_stream = AsyncStream(cast_to=None, response=None, client=client)
-    returned_stream._iterator = async_iterator(
-        [
-            MessageStartEvent(
-                message=Message(
-                    id="msg_0",
-                    content=[],
-                    model="claude-3-5-sonnet-20240620",
-                    role="assistant",
-                    stop_reason=None,
-                    stop_sequence=None,
-                    type="message",
-                    usage=Usage(input_tokens=366, output_tokens=10),
-                ),
-                type="message_start",
-            ),
-            ContentBlockStartEvent(
-                type="content_block_start",
-                index=0,
-                content_block=ToolUseBlock(
-                    id="toolu_0", input={}, name="get_weather", type="tool_use"
-                ),
-            ),
-            ContentBlockDeltaEvent(
-                delta=InputJSONDelta(partial_json="", type="input_json_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockDeltaEvent(
-                delta=InputJSONDelta(
-                    partial_json="{'location':", type="input_json_delta"
-                ),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockDeltaEvent(
-                delta=InputJSONDelta(partial_json=" 'S", type="input_json_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockDeltaEvent(
-                delta=InputJSONDelta(partial_json="an ", type="input_json_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockDeltaEvent(
-                delta=InputJSONDelta(
-                    partial_json="Francisco, C", type="input_json_delta"
-                ),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockDeltaEvent(
-                delta=InputJSONDelta(partial_json="A'}", type="input_json_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockStopEvent(type="content_block_stop", index=0),
-            MessageDeltaEvent(
-                delta=Delta(stop_reason="tool_use", stop_sequence=None),
-                usage=MessageDeltaUsage(output_tokens=41),
-                type="message_delta",
-            ),
-        ]
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=Message(
+                            id="msg_0",
+                            content=[],
+                            model="claude-3-5-sonnet-20240620",
+                            role="assistant",
+                            stop_reason=None,
+                            stop_sequence=None,
+                            type="message",
+                            usage=Usage(input_tokens=366, output_tokens=10),
+                        ),
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=ToolUseBlock(
+                            id="toolu_0", input={}, name="get_weather", type="tool_use"
+                        ),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(partial_json="", type="input_json_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(
+                            partial_json='{"location": "', type="input_json_delta"
+                        ),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(partial_json="S", type="input_json_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(
+                            partial_json="an ", type="input_json_delta"
+                        ),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(
+                            partial_json="Francisco, C", type="input_json_delta"
+                        ),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=InputJSONDelta(
+                            partial_json='A"}', type="input_json_delta"
+                        ),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockStopEvent(type="content_block_stop", index=0),
+                    MessageDeltaEvent(
+                        delta=Delta(stop_reason="tool_use", stop_sequence=None),
+                        usage=MessageDeltaUsage(output_tokens=41),
+                        type="message_delta",
+                    ),
+                ]
+            )
+        )
     )
 
     sentry_init(
@@ -637,7 +2107,6 @@ async def test_streaming_create_message_with_input_json_delta_async(
         send_default_pii=send_default_pii,
     )
     events = capture_events()
-    client.messages._post = AsyncMock(return_value=returned_stream)
 
     messages = [
         {
@@ -646,15 +2115,20 @@ async def test_streaming_create_message_with_input_json_delta_async(
         }
     ]
 
-    with start_transaction(name="anthropic"):
-        message = await client.messages.create(
-            max_tokens=1024, messages=messages, model="model", stream=True
-        )
-
-        async for _ in message:
-            pass
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            async with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+            ) as stream:
+                async for event in stream:
+                    pass
 
-    assert message == returned_stream
     assert len(events) == 1
     (event,) = events
 
@@ -666,6 +2140,7 @@ async def test_streaming_create_message_with_input_json_delta_async(
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
@@ -676,7 +2151,7 @@ async def test_streaming_create_message_with_input_json_delta_async(
         )
         assert (
             span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
-            == "{'location': 'San Francisco, CA'}"
+            == '{"location": "San Francisco, CA"}'
         )
 
     else:
@@ -730,6 +2205,7 @@ def test_span_status_error(sentry_init, capture_events):
     assert transaction["spans"][0]["status"] == "internal_error"
     assert transaction["spans"][0]["tags"]["status"] == "internal_error"
     assert transaction["contexts"]["trace"]["status"] == "internal_error"
+    assert transaction["spans"][0]["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert transaction["spans"][0]["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
 
 
@@ -755,6 +2231,7 @@ async def test_span_status_error_async(sentry_init, capture_events):
     assert transaction["spans"][0]["status"] == "internal_error"
     assert transaction["spans"][0]["tags"]["status"] == "internal_error"
     assert transaction["contexts"]["trace"]["status"] == "internal_error"
+    assert transaction["spans"][0]["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert transaction["spans"][0]["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
 
 
@@ -803,6 +2280,7 @@ def test_span_origin(sentry_init, capture_events):
 
     assert event["contexts"]["trace"]["origin"] == "manual"
     assert event["spans"][0]["origin"] == "auto.ai.anthropic"
+    assert event["spans"][0]["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert event["spans"][0]["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
 
 
@@ -831,6 +2309,7 @@ async def test_span_origin_async(sentry_init, capture_events):
 
     assert event["contexts"]["trace"]["origin"] == "manual"
     assert event["spans"][0]["origin"] == "auto.ai.anthropic"
+    assert event["spans"][0]["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert event["spans"][0]["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
 
 
@@ -852,13 +2331,15 @@ def test_collect_ai_data_with_input_json_delta():
 
     content_blocks = []
 
-    model, new_usage, new_content_blocks = _collect_ai_data(
+    model, new_usage, new_content_blocks, response_id, finish_reason = _collect_ai_data(
         event, model, usage, content_blocks
     )
     assert model is None
     assert new_usage.input_tokens == usage.input_tokens
     assert new_usage.output_tokens == usage.output_tokens
     assert new_content_blocks == ["test"]
+    assert response_id is None
+    assert finish_reason is None
 
 
 @pytest.mark.skipif(
@@ -951,6 +2432,7 @@ def mock_messages_create(*args, **kwargs):
 
     # Verify that the span was created correctly
     assert span["op"] == "gen_ai.chat"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span["data"]
 
@@ -996,6 +2478,7 @@ def test_anthropic_message_truncation(sentry_init, capture_events):
     assert len(chat_spans) > 0
 
     chat_span = chat_spans[0]
+    assert chat_span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert chat_span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert SPANDATA.GEN_AI_REQUEST_MESSAGES in chat_span["data"]
 
@@ -1047,6 +2530,7 @@ async def test_anthropic_message_truncation_async(sentry_init, capture_events):
     assert len(chat_spans) > 0
 
     chat_span = chat_spans[0]
+    assert chat_span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert chat_span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert SPANDATA.GEN_AI_REQUEST_MESSAGES in chat_span["data"]
 
@@ -1058,9 +2542,95 @@ async def test_anthropic_message_truncation_async(sentry_init, capture_events):
     assert len(parsed_messages) == 1
     assert "small message 5" in str(parsed_messages[0])
 
-    assert tx["_meta"]["spans"]["0"]["data"]["gen_ai.request.messages"][""]["len"] == 5
+    assert tx["_meta"]["spans"]["0"]["data"]["gen_ai.request.messages"][""]["len"] == 5
+
+
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+def test_nonstreaming_create_message_with_system_prompt(
+    sentry_init, capture_events, send_default_pii, include_prompts
+):
+    """Test that system prompts are properly captured in GEN_AI_REQUEST_MESSAGES."""
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=include_prompts)],
+        traces_sample_rate=1.0,
+        send_default_pii=send_default_pii,
+    )
+    events = capture_events()
+    client = Anthropic(api_key="z")
+    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with start_transaction(name="anthropic"):
+        response = client.messages.create(
+            max_tokens=1024,
+            messages=messages,
+            model="model",
+            system="You are a helpful assistant.",
+        )
+
+    assert response == EXAMPLE_MESSAGE
+    usage = response.usage
+
+    assert usage.input_tokens == 10
+    assert usage.output_tokens == 20
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    assert len(event["spans"]) == 1
+    (span,) = event["spans"]
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    if send_default_pii and include_prompts:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS in span["data"]
+        system_instructions = json.loads(
+            span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]
+        )
+        assert system_instructions == [
+            {"type": "text", "content": "You are a helpful assistant."}
+        ]
+
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span["data"]
+        stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+        assert len(stored_messages) == 1
+        assert stored_messages[0]["role"] == "user"
+        assert stored_messages[0]["content"] == "Hello, Claude"
+        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi, I'm Claude."
+    else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is False
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS] == ["end_turn"]
 
 
+@pytest.mark.asyncio
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [
@@ -1070,18 +2640,18 @@ async def test_anthropic_message_truncation_async(sentry_init, capture_events):
         (False, False),
     ],
 )
-def test_nonstreaming_create_message_with_system_prompt(
+async def test_nonstreaming_create_message_with_system_prompt_async(
     sentry_init, capture_events, send_default_pii, include_prompts
 ):
-    """Test that system prompts are properly captured in GEN_AI_REQUEST_MESSAGES."""
+    """Test that system prompts are properly captured in GEN_AI_REQUEST_MESSAGES (async)."""
     sentry_init(
         integrations=[AnthropicIntegration(include_prompts=include_prompts)],
         traces_sample_rate=1.0,
         send_default_pii=send_default_pii,
     )
     events = capture_events()
-    client = Anthropic(api_key="z")
-    client.messages._post = mock.Mock(return_value=EXAMPLE_MESSAGE)
+    client = AsyncAnthropic(api_key="z")
+    client.messages._post = AsyncMock(return_value=EXAMPLE_MESSAGE)
 
     messages = [
         {
@@ -1091,7 +2661,7 @@ def test_nonstreaming_create_message_with_system_prompt(
     ]
 
     with start_transaction(name="anthropic"):
-        response = client.messages.create(
+        response = await client.messages.create(
             max_tokens=1024,
             messages=messages,
             model="model",
@@ -1115,6 +2685,7 @@ def test_nonstreaming_create_message_with_system_prompt(
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
@@ -1142,9 +2713,9 @@ def test_nonstreaming_create_message_with_system_prompt(
     assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
     assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
     assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is False
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS] == ["end_turn"]
 
 
-@pytest.mark.asyncio
 @pytest.mark.parametrize(
     "send_default_pii, include_prompts",
     [
@@ -1154,18 +2725,60 @@ def test_nonstreaming_create_message_with_system_prompt(
         (False, False),
     ],
 )
-async def test_nonstreaming_create_message_with_system_prompt_async(
-    sentry_init, capture_events, send_default_pii, include_prompts
+def test_streaming_create_message_with_system_prompt(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    server_side_event_chunks,
 ):
-    """Test that system prompts are properly captured in GEN_AI_REQUEST_MESSAGES (async)."""
+    """Test that system prompts are properly captured in streaming mode."""
+    client = Anthropic(api_key="z")
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=EXAMPLE_MESSAGE,
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=TextBlock(type="text", text=""),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="Hi", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockStopEvent(type="content_block_stop", index=0),
+                MessageDeltaEvent(
+                    delta=Delta(),
+                    usage=MessageDeltaUsage(output_tokens=10),
+                    type="message_delta",
+                ),
+            ]
+        )
+    )
+
     sentry_init(
         integrations=[AnthropicIntegration(include_prompts=include_prompts)],
         traces_sample_rate=1.0,
         send_default_pii=send_default_pii,
     )
     events = capture_events()
-    client = AsyncAnthropic(api_key="z")
-    client.messages._post = AsyncMock(return_value=EXAMPLE_MESSAGE)
 
     messages = [
         {
@@ -1174,19 +2787,22 @@ async def test_nonstreaming_create_message_with_system_prompt_async(
         }
     ]
 
-    with start_transaction(name="anthropic"):
-        response = await client.messages.create(
-            max_tokens=1024,
-            messages=messages,
-            model="model",
-            system="You are a helpful assistant.",
-        )
-
-    assert response == EXAMPLE_MESSAGE
-    usage = response.usage
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            message = client.messages.create(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+                stream=True,
+                system="You are a helpful assistant.",
+            )
 
-    assert usage.input_tokens == 10
-    assert usage.output_tokens == 20
+            for _ in message:
+                pass
 
     assert len(events) == 1
     (event,) = events
@@ -1199,6 +2815,7 @@ async def test_nonstreaming_create_message_with_system_prompt_async(
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
@@ -1216,16 +2833,17 @@ async def test_nonstreaming_create_message_with_system_prompt_async(
         assert len(stored_messages) == 1
         assert stored_messages[0]["role"] == "user"
         assert stored_messages[0]["content"] == "Hello, Claude"
-        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi, I'm Claude."
+        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
+
     else:
         assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
         assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
         assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
 
     assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
-    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 20
-    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 30
-    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is False
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
 
 
 @pytest.mark.parametrize(
@@ -1237,44 +2855,53 @@ async def test_nonstreaming_create_message_with_system_prompt_async(
         (False, False),
     ],
 )
-def test_streaming_create_message_with_system_prompt(
-    sentry_init, capture_events, send_default_pii, include_prompts
+def test_stream_messages_with_system_prompt(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    server_side_event_chunks,
 ):
     """Test that system prompts are properly captured in streaming mode."""
     client = Anthropic(api_key="z")
-    returned_stream = Stream(cast_to=None, response=None, client=client)
-    returned_stream._iterator = [
-        MessageStartEvent(
-            message=EXAMPLE_MESSAGE,
-            type="message_start",
-        ),
-        ContentBlockStartEvent(
-            type="content_block_start",
-            index=0,
-            content_block=TextBlock(type="text", text=""),
-        ),
-        ContentBlockDeltaEvent(
-            delta=TextDelta(text="Hi", type="text_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockDeltaEvent(
-            delta=TextDelta(text="!", type="text_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockDeltaEvent(
-            delta=TextDelta(text=" I'm Claude!", type="text_delta"),
-            index=0,
-            type="content_block_delta",
-        ),
-        ContentBlockStopEvent(type="content_block_stop", index=0),
-        MessageDeltaEvent(
-            delta=Delta(),
-            usage=MessageDeltaUsage(output_tokens=10),
-            type="message_delta",
-        ),
-    ]
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    message=EXAMPLE_MESSAGE,
+                    type="message_start",
+                ),
+                ContentBlockStartEvent(
+                    type="content_block_start",
+                    index=0,
+                    content_block=TextBlock(type="text", text=""),
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="Hi", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text="!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockDeltaEvent(
+                    delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                    index=0,
+                    type="content_block_delta",
+                ),
+                ContentBlockStopEvent(type="content_block_stop", index=0),
+                MessageDeltaEvent(
+                    delta=Delta(),
+                    usage=MessageDeltaUsage(output_tokens=10),
+                    type="message_delta",
+                ),
+            ]
+        )
+    )
 
     sentry_init(
         integrations=[AnthropicIntegration(include_prompts=include_prompts)],
@@ -1282,7 +2909,6 @@ def test_streaming_create_message_with_system_prompt(
         send_default_pii=send_default_pii,
     )
     events = capture_events()
-    client.messages._post = mock.Mock(return_value=returned_stream)
 
     messages = [
         {
@@ -1291,19 +2917,153 @@ def test_streaming_create_message_with_system_prompt(
         }
     ]
 
-    with start_transaction(name="anthropic"):
-        message = client.messages.create(
-            max_tokens=1024,
-            messages=messages,
-            model="model",
-            stream=True,
-            system="You are a helpful assistant.",
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+                system="You are a helpful assistant.",
+            ) as stream:
+                for event in stream:
+                    pass
+
+    assert len(events) == 1
+    (event,) = events
+
+    assert event["type"] == "transaction"
+    assert event["transaction"] == "anthropic"
+
+    assert len(event["spans"]) == 1
+    (span,) = event["spans"]
+
+    assert span["op"] == OP.GEN_AI_CHAT
+    assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
+    assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
+    assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
+
+    if send_default_pii and include_prompts:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS in span["data"]
+        system_instructions = json.loads(
+            span["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS]
+        )
+        assert system_instructions == [
+            {"type": "text", "content": "You are a helpful assistant."}
+        ]
+
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES in span["data"]
+        stored_messages = json.loads(span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES])
+        assert len(stored_messages) == 1
+        assert stored_messages[0]["role"] == "user"
+        assert stored_messages[0]["content"] == "Hello, Claude"
+        assert span["data"][SPANDATA.GEN_AI_RESPONSE_TEXT] == "Hi! I'm Claude!"
+
+    else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in span["data"]
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in span["data"]
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in span["data"]
+
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 20
+    assert span["data"][SPANDATA.GEN_AI_RESPONSE_STREAMING] is True
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+async def test_stream_message_with_system_prompt_async(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
+):
+    """Test that system prompts are properly captured in streaming mode (async)."""
+    client = AsyncAnthropic(api_key="z")
+
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=EXAMPLE_MESSAGE,
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=TextBlock(type="text", text=""),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="Hi", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockStopEvent(type="content_block_stop", index=0),
+                    MessageDeltaEvent(
+                        delta=Delta(),
+                        usage=MessageDeltaUsage(output_tokens=10),
+                        type="message_delta",
+                    ),
+                ]
+            )
         )
+    )
+
+    sentry_init(
+        integrations=[AnthropicIntegration(include_prompts=include_prompts)],
+        traces_sample_rate=1.0,
+        send_default_pii=send_default_pii,
+    )
+    events = capture_events()
 
-        for _ in message:
-            pass
+    messages = [
+        {
+            "role": "user",
+            "content": "Hello, Claude",
+        }
+    ]
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            async with client.messages.stream(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+                system="You are a helpful assistant.",
+            ) as stream:
+                async for event in stream:
+                    pass
 
-    assert message == returned_stream
     assert len(events) == 1
     (event,) = events
 
@@ -1315,6 +3075,7 @@ def test_streaming_create_message_with_system_prompt(
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
@@ -1356,44 +3117,54 @@ def test_streaming_create_message_with_system_prompt(
     ],
 )
 async def test_streaming_create_message_with_system_prompt_async(
-    sentry_init, capture_events, send_default_pii, include_prompts, async_iterator
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
 ):
     """Test that system prompts are properly captured in streaming mode (async)."""
     client = AsyncAnthropic(api_key="z")
-    returned_stream = AsyncStream(cast_to=None, response=None, client=client)
-    returned_stream._iterator = async_iterator(
-        [
-            MessageStartEvent(
-                message=EXAMPLE_MESSAGE,
-                type="message_start",
-            ),
-            ContentBlockStartEvent(
-                type="content_block_start",
-                index=0,
-                content_block=TextBlock(type="text", text=""),
-            ),
-            ContentBlockDeltaEvent(
-                delta=TextDelta(text="Hi", type="text_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockDeltaEvent(
-                delta=TextDelta(text="!", type="text_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockDeltaEvent(
-                delta=TextDelta(text=" I'm Claude!", type="text_delta"),
-                index=0,
-                type="content_block_delta",
-            ),
-            ContentBlockStopEvent(type="content_block_stop", index=0),
-            MessageDeltaEvent(
-                delta=Delta(),
-                usage=MessageDeltaUsage(output_tokens=10),
-                type="message_delta",
-            ),
-        ]
+
+    response = get_model_response(
+        async_iterator(
+            server_side_event_chunks(
+                [
+                    MessageStartEvent(
+                        message=EXAMPLE_MESSAGE,
+                        type="message_start",
+                    ),
+                    ContentBlockStartEvent(
+                        type="content_block_start",
+                        index=0,
+                        content_block=TextBlock(type="text", text=""),
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="Hi", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text="!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockDeltaEvent(
+                        delta=TextDelta(text=" I'm Claude!", type="text_delta"),
+                        index=0,
+                        type="content_block_delta",
+                    ),
+                    ContentBlockStopEvent(type="content_block_stop", index=0),
+                    MessageDeltaEvent(
+                        delta=Delta(),
+                        usage=MessageDeltaUsage(output_tokens=10),
+                        type="message_delta",
+                    ),
+                ]
+            )
+        )
     )
 
     sentry_init(
@@ -1402,7 +3173,6 @@ async def test_streaming_create_message_with_system_prompt_async(
         send_default_pii=send_default_pii,
     )
     events = capture_events()
-    client.messages._post = AsyncMock(return_value=returned_stream)
 
     messages = [
         {
@@ -1411,19 +3181,23 @@ async def test_streaming_create_message_with_system_prompt_async(
         }
     ]
 
-    with start_transaction(name="anthropic"):
-        message = await client.messages.create(
-            max_tokens=1024,
-            messages=messages,
-            model="model",
-            stream=True,
-            system="You are a helpful assistant.",
-        )
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            message = await client.messages.create(
+                max_tokens=1024,
+                messages=messages,
+                model="model",
+                stream=True,
+                system="You are a helpful assistant.",
+            )
 
-        async for _ in message:
-            pass
+            async for _ in message:
+                pass
 
-    assert message == returned_stream
     assert len(events) == 1
     (event,) = events
 
@@ -1435,6 +3209,7 @@ async def test_streaming_create_message_with_system_prompt_async(
 
     assert span["op"] == OP.GEN_AI_CHAT
     assert span["description"] == "chat model"
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
     assert span["data"][SPANDATA.GEN_AI_REQUEST_MODEL] == "model"
 
@@ -1501,6 +3276,7 @@ def test_system_prompt_with_complex_structure(sentry_init, capture_events):
     assert len(event["spans"]) == 1
     (span,) = event["spans"]
 
+    assert span["data"][SPANDATA.GEN_AI_SYSTEM] == "anthropic"
     assert span["data"][SPANDATA.GEN_AI_OPERATION_NAME] == "chat"
 
     assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS in span["data"]
@@ -2360,50 +4136,129 @@ def test_input_tokens_include_cache_read_nonstreaming(sentry_init, capture_event
     assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHE_WRITE] == 0
 
 
-def test_input_tokens_include_cache_read_streaming(sentry_init, capture_events):
+def test_input_tokens_include_cache_read_streaming(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    server_side_event_chunks,
+):
     """
     Test that gen_ai.usage.input_tokens includes cache_read tokens (streaming).
 
     Same cache-hit scenario as non-streaming, using realistic streaming events.
     """
     client = Anthropic(api_key="z")
-    returned_stream = Stream(cast_to=None, response=None, client=client)
-    returned_stream._iterator = [
-        MessageStartEvent(
-            type="message_start",
-            message=Message(
-                id="id",
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    type="message_start",
+                    message=Message(
+                        id="id",
+                        model="claude-sonnet-4-20250514",
+                        role="assistant",
+                        content=[],
+                        type="message",
+                        usage=Usage(
+                            input_tokens=19,
+                            output_tokens=0,
+                            cache_read_input_tokens=2846,
+                            cache_creation_input_tokens=0,
+                        ),
+                    ),
+                ),
+                MessageDeltaEvent(
+                    type="message_delta",
+                    delta=Delta(stop_reason="end_turn"),
+                    usage=MessageDeltaUsage(output_tokens=14),
+                ),
+            ]
+        )
+    )
+
+    sentry_init(integrations=[AnthropicIntegration()], traces_sample_rate=1.0)
+    events = capture_events()
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            for _ in client.messages.create(
+                max_tokens=1024,
+                messages=[{"role": "user", "content": "What is 5+5?"}],
                 model="claude-sonnet-4-20250514",
-                role="assistant",
-                content=[],
-                type="message",
-                usage=Usage(
-                    input_tokens=19,
-                    output_tokens=0,
-                    cache_read_input_tokens=2846,
-                    cache_creation_input_tokens=0,
+                stream=True,
+            ):
+                pass
+
+    (span,) = events[0]["spans"]
+
+    # input_tokens should be total: 19 + 2846 = test_stream_messages_input_tokens_include_cache_read_streaming
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 2865
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 2879  # 2865 + 14
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHED] == 2846
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHE_WRITE] == 0
+
+
+def test_stream_messages_input_tokens_include_cache_read_streaming(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    server_side_event_chunks,
+):
+    """
+    Test that gen_ai.usage.input_tokens includes cache_read tokens (streaming).
+
+    Same cache-hit scenario as non-streaming, using realistic streaming events.
+    """
+    client = Anthropic(api_key="z")
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    type="message_start",
+                    message=Message(
+                        id="id",
+                        model="claude-sonnet-4-20250514",
+                        role="assistant",
+                        content=[],
+                        type="message",
+                        usage=Usage(
+                            input_tokens=19,
+                            output_tokens=0,
+                            cache_read_input_tokens=2846,
+                            cache_creation_input_tokens=0,
+                        ),
+                    ),
                 ),
-            ),
-        ),
-        MessageDeltaEvent(
-            type="message_delta",
-            delta=Delta(stop_reason="end_turn"),
-            usage=MessageDeltaUsage(output_tokens=14),
-        ),
-    ]
+                MessageDeltaEvent(
+                    type="message_delta",
+                    delta=Delta(stop_reason="end_turn"),
+                    usage=MessageDeltaUsage(output_tokens=14),
+                ),
+            ]
+        )
+    )
 
     sentry_init(integrations=[AnthropicIntegration()], traces_sample_rate=1.0)
     events = capture_events()
-    client.messages._post = mock.Mock(return_value=returned_stream)
 
-    with start_transaction(name="anthropic"):
-        for _ in client.messages.create(
-            max_tokens=1024,
-            messages=[{"role": "user", "content": "What is 5+5?"}],
-            model="claude-sonnet-4-20250514",
-            stream=True,
-        ):
-            pass
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            with client.messages.stream(
+                max_tokens=1024,
+                messages=[{"role": "user", "content": "What is 5+5?"}],
+                model="claude-sonnet-4-20250514",
+            ) as stream:
+                for event in stream:
+                    pass
 
     (span,) = events[0]["spans"]
 
@@ -2452,46 +4307,119 @@ def test_input_tokens_unchanged_without_caching(sentry_init, capture_events):
     assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 32  # 20 + 12
 
 
-def test_cache_tokens_streaming(sentry_init, capture_events):
+def test_cache_tokens_streaming(
+    sentry_init,
+    capture_events,
+    get_model_response,
+    server_side_event_chunks,
+):
     """Test cache tokens are tracked for streaming responses."""
     client = Anthropic(api_key="z")
-    returned_stream = Stream(cast_to=None, response=None, client=client)
-    returned_stream._iterator = [
-        MessageStartEvent(
-            type="message_start",
-            message=Message(
-                id="id",
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    type="message_start",
+                    message=Message(
+                        id="id",
+                        model="claude-3-5-sonnet-20241022",
+                        role="assistant",
+                        content=[],
+                        type="message",
+                        usage=Usage(
+                            input_tokens=100,
+                            output_tokens=0,
+                            cache_read_input_tokens=80,
+                            cache_creation_input_tokens=20,
+                        ),
+                    ),
+                ),
+                MessageDeltaEvent(
+                    type="message_delta",
+                    delta=Delta(stop_reason="end_turn"),
+                    usage=MessageDeltaUsage(output_tokens=10),
+                ),
+            ]
+        )
+    )
+
+    sentry_init(integrations=[AnthropicIntegration()], traces_sample_rate=1.0)
+    events = capture_events()
+
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            for _ in client.messages.create(
+                max_tokens=1024,
+                messages=[{"role": "user", "content": "Hello"}],
                 model="claude-3-5-sonnet-20241022",
-                role="assistant",
-                content=[],
-                type="message",
-                usage=Usage(
-                    input_tokens=100,
-                    output_tokens=0,
-                    cache_read_input_tokens=80,
-                    cache_creation_input_tokens=20,
+                stream=True,
+            ):
+                pass
+
+    (span,) = events[0]["spans"]
+    # input_tokens normalized: 100 + 80 (cache_read) + 20 (cache_write) = 200
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS] == 200
+    assert span["data"][SPANDATA.GEN_AI_USAGE_OUTPUT_TOKENS] == 10
+    assert span["data"][SPANDATA.GEN_AI_USAGE_TOTAL_TOKENS] == 210
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHED] == 80
+    assert span["data"][SPANDATA.GEN_AI_USAGE_INPUT_TOKENS_CACHE_WRITE] == 20
+
+
+def test_stream_messages_cache_tokens(
+    sentry_init, capture_events, get_model_response, server_side_event_chunks
+):
+    """Test cache tokens are tracked for streaming responses."""
+    client = Anthropic(api_key="z")
+
+    response = get_model_response(
+        server_side_event_chunks(
+            [
+                MessageStartEvent(
+                    type="message_start",
+                    message=Message(
+                        id="id",
+                        model="claude-3-5-sonnet-20241022",
+                        role="assistant",
+                        content=[],
+                        type="message",
+                        usage=Usage(
+                            input_tokens=100,
+                            output_tokens=0,
+                            cache_read_input_tokens=80,
+                            cache_creation_input_tokens=20,
+                        ),
+                    ),
                 ),
-            ),
-        ),
-        MessageDeltaEvent(
-            type="message_delta",
-            delta=Delta(stop_reason="end_turn"),
-            usage=MessageDeltaUsage(output_tokens=10),
-        ),
-    ]
+                MessageDeltaEvent(
+                    type="message_delta",
+                    delta=Delta(stop_reason="end_turn"),
+                    usage=MessageDeltaUsage(output_tokens=10),
+                ),
+            ]
+        )
+    )
 
     sentry_init(integrations=[AnthropicIntegration()], traces_sample_rate=1.0)
     events = capture_events()
-    client.messages._post = mock.Mock(return_value=returned_stream)
 
-    with start_transaction(name="anthropic"):
-        for _ in client.messages.create(
-            max_tokens=1024,
-            messages=[{"role": "user", "content": "Hello"}],
-            model="claude-3-5-sonnet-20241022",
-            stream=True,
-        ):
-            pass
+    with mock.patch.object(
+        client._client,
+        "send",
+        return_value=response,
+    ) as _:
+        with start_transaction(name="anthropic"):
+            with client.messages.stream(
+                max_tokens=1024,
+                messages=[{"role": "user", "content": "Hello"}],
+                model="claude-3-5-sonnet-20241022",
+            ) as stream:
+                for event in stream:
+                    pass
 
     (span,) = events[0]["spans"]
     # input_tokens normalized: 100 + 80 (cache_read) + 20 (cache_write) = 200
diff --git a/tests/integrations/asyncpg/test_asyncpg.py b/tests/integrations/asyncpg/test_asyncpg.py
index e23612c055..62b5f166f7 100644
--- a/tests/integrations/asyncpg/test_asyncpg.py
+++ b/tests/integrations/asyncpg/test_asyncpg.py
@@ -463,10 +463,7 @@ async def test_connection_pool(sentry_init, capture_events) -> None:
         {
             "category": "query",
             "data": {},
-            "message": "SELECT pg_advisory_unlock_all();\n"
-            "CLOSE ALL;\n"
-            "UNLISTEN *;\n"
-            "RESET ALL;",
+            "message": "SELECT pg_advisory_unlock_all(); CLOSE ALL; UNLISTEN *; RESET ALL;",
             "type": "default",
         },
         {
@@ -478,10 +475,7 @@ async def test_connection_pool(sentry_init, capture_events) -> None:
         {
             "category": "query",
             "data": {},
-            "message": "SELECT pg_advisory_unlock_all();\n"
-            "CLOSE ALL;\n"
-            "UNLISTEN *;\n"
-            "RESET ALL;",
+            "message": "SELECT pg_advisory_unlock_all(); CLOSE ALL; UNLISTEN *; RESET ALL;",
             "type": "default",
         },
     ]
@@ -786,3 +780,79 @@ async def test_span_origin(sentry_init, capture_events):
 
     for span in event["spans"]:
         assert span["origin"] == "auto.db.asyncpg"
+
+
+@pytest.mark.asyncio
+async def test_multiline_query_description_normalized(sentry_init, capture_events):
+    sentry_init(
+        integrations=[AsyncPGIntegration()],
+        traces_sample_rate=1.0,
+    )
+    events = capture_events()
+
+    with start_transaction(name="test_transaction"):
+        conn: Connection = await connect(PG_CONNECTION_URI)
+        await conn.execute(
+            """
+            SELECT
+                id,
+                name
+            FROM
+                users
+            WHERE
+                name = 'Alice'
+            """
+        )
+        await conn.close()
+
+    (event,) = events
+
+    spans = [
+        s
+        for s in event["spans"]
+        if s["op"] == "db" and "SELECT" in s.get("description", "")
+    ]
+    assert len(spans) == 1
+    assert spans[0]["description"] == "SELECT id, name FROM users WHERE name = 'Alice'"
+
+
+@pytest.mark.asyncio
+async def test_before_send_transaction_sees_normalized_description(
+    sentry_init, capture_events
+):
+    def before_send_transaction(event, hint):
+        for span in event.get("spans", []):
+            desc = span.get("description", "")
+            if "SELECT id, name FROM users" in desc:
+                span["description"] = "filtered"
+        return event
+
+    sentry_init(
+        integrations=[AsyncPGIntegration()],
+        traces_sample_rate=1.0,
+        before_send_transaction=before_send_transaction,
+    )
+    events = capture_events()
+
+    with start_transaction(name="test_transaction"):
+        conn: Connection = await connect(PG_CONNECTION_URI)
+        await conn.execute(
+            """
+            SELECT
+                id,
+                name
+            FROM
+                users
+            """
+        )
+        await conn.close()
+
+    (event,) = events
+    spans = [
+        s
+        for s in event["spans"]
+        if s["op"] == "db" and "filtered" in s.get("description", "")
+    ]
+
+    assert len(spans) == 1
+    assert spans[0]["description"] == "filtered"
diff --git a/tests/integrations/django/test_tasks.py b/tests/integrations/django/test_tasks.py
index 220d64b111..56c68b807f 100644
--- a/tests/integrations/django/test_tasks.py
+++ b/tests/integrations/django/test_tasks.py
@@ -1,7 +1,6 @@
 import pytest
 
 import sentry_sdk
-from sentry_sdk import start_span
 from sentry_sdk.integrations.django import DjangoIntegration
 from sentry_sdk.consts import OP
 
diff --git a/tests/integrations/google_genai/test_google_genai.py b/tests/integrations/google_genai/test_google_genai.py
index 68ae9d234f..207887860f 100644
--- a/tests/integrations/google_genai/test_google_genai.py
+++ b/tests/integrations/google_genai/test_google_genai.py
@@ -729,6 +729,39 @@ def test_empty_response(sentry_init, capture_events, mock_genai_client):
     assert len(event["spans"]) == 1
 
 
+def test_response_with_none_parts(sentry_init, capture_events, mock_genai_client):
+    """Test handling of candidates where content.parts is explicitly None.
+
+    Regression test for https://github.com/getsentry/sentry-python/issues/5854
+    """
+    sentry_init(
+        integrations=[GoogleGenAIIntegration()],
+        traces_sample_rate=1.0,
+    )
+    events = capture_events()
+
+    # Candidate with content present but parts set to None
+    minimal_response_json = {
+        "candidates": [{"content": {"role": "model", "parts": None}}]
+    }
+    mock_http_response = create_mock_http_response(minimal_response_json)
+
+    with mock.patch.object(
+        mock_genai_client._api_client, "request", return_value=mock_http_response
+    ):
+        with start_transaction(name="google_genai"):
+            response = mock_genai_client.models.generate_content(
+                model="gemini-1.5-flash", contents="Test", config=create_test_config()
+            )
+
+    assert response is not None
+    assert response.candidates[0].content.parts is None
+
+    (event,) = events
+    # Should not raise TypeError: 'NoneType' object is not iterable
+    assert len(event["spans"]) == 1
+
+
 def test_response_with_different_id_fields(
     sentry_init, capture_events, mock_genai_client
 ):
diff --git a/tests/integrations/huggingface_hub/test_huggingface_hub.py b/tests/integrations/huggingface_hub/test_huggingface_hub.py
index 851c1f717a..d17a7a31ef 100644
--- a/tests/integrations/huggingface_hub/test_huggingface_hub.py
+++ b/tests/integrations/huggingface_hub/test_huggingface_hub.py
@@ -2,7 +2,6 @@
 import pytest
 import re
 import responses
-import httpx
 
 from huggingface_hub import InferenceClient
 
diff --git a/tests/integrations/langchain/test_langchain.py b/tests/integrations/langchain/test_langchain.py
index 8a8d646113..24d7619145 100644
--- a/tests/integrations/langchain/test_langchain.py
+++ b/tests/integrations/langchain/test_langchain.py
@@ -9,9 +9,10 @@
 
 try:
     # Langchain >= 0.2
-    from langchain_openai import ChatOpenAI
+    from langchain_openai import ChatOpenAI, OpenAI
 except ImportError:
     # Langchain < 0.2
+    from langchain_community.llms import OpenAI
     from langchain_community.chat_models import ChatOpenAI
 
 from langchain_core.callbacks import BaseCallbackManager, CallbackManagerForLLMRun
@@ -22,6 +23,7 @@
 
 import sentry_sdk
 from sentry_sdk import start_transaction
+from sentry_sdk.utils import package_version
 from sentry_sdk.integrations.langchain import (
     LangchainIntegration,
     SentryLangchainCallback,
@@ -32,12 +34,39 @@
 try:
     # langchain v1+
     from langchain.tools import tool
+    from langchain.agents import create_agent
     from langchain_classic.agents import AgentExecutor, create_openai_tools_agent  # type: ignore[import-not-found]
 except ImportError:
     # langchain <v1
     from langchain.agents import tool, AgentExecutor, create_openai_tools_agent
 
 from langchain_core.prompts import ChatPromptTemplate, MessagesPlaceholder
+from langchain_core.messages import HumanMessage, SystemMessage
+
+from openai.types.chat.chat_completion_chunk import (
+    ChatCompletionChunk,
+    Choice,
+    ChoiceDelta,
+    ChoiceDeltaToolCall,
+    ChoiceDeltaToolCallFunction,
+)
+
+from openai.types.completion import Completion
+from openai.types.completion_choice import CompletionChoice
+
+from openai.types.completion_usage import (
+    CompletionUsage,
+)
+
+from openai.types.responses import (
+    ResponseUsage,
+)
+from openai.types.responses.response_usage import (
+    InputTokensDetails,
+    OutputTokensDetails,
+)
+
+LANGCHAIN_VERSION = package_version("langchain")
 
 
 @tool
@@ -66,13 +95,381 @@ def _llm_type(self) -> str:
         return llm_type
 
 
+def test_langchain_text_completion(
+    sentry_init,
+    capture_events,
+    get_model_response,
+):
+    sentry_init(
+        integrations=[
+            LangchainIntegration(
+                include_prompts=True,
+            )
+        ],
+        traces_sample_rate=1.0,
+        send_default_pii=True,
+    )
+    events = capture_events()
+
+    model_response = get_model_response(
+        Completion(
+            id="completion-id",
+            object="text_completion",
+            created=10000000,
+            model="gpt-3.5-turbo",
+            choices=[
+                CompletionChoice(
+                    index=0,
+                    finish_reason="stop",
+                    text="The capital of France is Paris.",
+                )
+            ],
+            usage=CompletionUsage(
+                prompt_tokens=10,
+                completion_tokens=15,
+                total_tokens=25,
+            ),
+        ),
+        serialize_pydantic=True,
+    )
+
+    model = OpenAI(
+        model_name="gpt-3.5-turbo",
+        temperature=0.7,
+        max_tokens=100,
+        openai_api_key="badkey",
+    )
+
+    with patch.object(
+        model.client._client._client,
+        "send",
+        return_value=model_response,
+    ) as _:
+        with start_transaction():
+            input_text = "What is the capital of France?"
+            model.invoke(input_text, config={"run_name": "my-snazzy-pipeline"})
+
+    tx = events[0]
+    assert tx["type"] == "transaction"
+
+    llm_spans = [
+        span for span in tx.get("spans", []) if span.get("op") == "gen_ai.generate_text"
+    ]
+    assert len(llm_spans) > 0
+
+    llm_span = llm_spans[0]
+    assert llm_span["description"] == "generate_text gpt-3.5-turbo"
+    assert llm_span["data"]["gen_ai.system"] == "openai"
+    assert llm_span["data"]["gen_ai.pipeline.name"] == "my-snazzy-pipeline"
+    assert llm_span["data"]["gen_ai.request.model"] == "gpt-3.5-turbo"
+    assert llm_span["data"]["gen_ai.response.text"] == "The capital of France is Paris."
+    assert llm_span["data"]["gen_ai.usage.total_tokens"] == 25
+    assert llm_span["data"]["gen_ai.usage.input_tokens"] == 10
+    assert llm_span["data"]["gen_ai.usage.output_tokens"] == 15
+
+
+@pytest.mark.skipif(
+    LANGCHAIN_VERSION < (1,),
+    reason="LangChain 1.0+ required (ONE AGENT refactor)",
+)
 @pytest.mark.parametrize(
-    "send_default_pii, include_prompts, use_unknown_llm_type",
+    "send_default_pii, include_prompts",
     [
-        (True, True, False),
-        (True, False, False),
-        (False, True, False),
-        (False, False, True),
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+@pytest.mark.parametrize(
+    "system_instructions_content",
+    [
+        "You are very powerful assistant, but don't know current events",
+        [
+            {"type": "text", "text": "You are a helpful assistant."},
+            {"type": "text", "text": "Be concise and clear."},
+        ],
+    ],
+    ids=["string", "blocks"],
+)
+def test_langchain_create_agent(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    system_instructions_content,
+    request,
+    get_model_response,
+    nonstreaming_responses_model_response,
+):
+    sentry_init(
+        integrations=[
+            LangchainIntegration(
+                include_prompts=include_prompts,
+            )
+        ],
+        traces_sample_rate=1.0,
+        send_default_pii=send_default_pii,
+    )
+    events = capture_events()
+
+    model_response = get_model_response(
+        nonstreaming_responses_model_response,
+        serialize_pydantic=True,
+        request_headers={
+            "X-Stainless-Raw-Response": "True",
+        },
+    )
+
+    llm = ChatOpenAI(
+        model_name="gpt-3.5-turbo",
+        temperature=0,
+        openai_api_key="badkey",
+        use_responses_api=True,
+    )
+    agent = create_agent(
+        model=llm,
+        tools=[get_word_length],
+        system_prompt=SystemMessage(content=system_instructions_content),
+        name="word_length_agent",
+    )
+
+    with patch.object(
+        llm.client._client._client,
+        "send",
+        return_value=model_response,
+    ) as _:
+        with start_transaction():
+            agent.invoke(
+                {
+                    "messages": [
+                        HumanMessage(content="How many letters in the word eudca"),
+                    ],
+                },
+            )
+
+    tx = events[0]
+    assert tx["type"] == "transaction"
+    assert tx["contexts"]["trace"]["origin"] == "manual"
+
+    chat_spans = list(x for x in tx["spans"] if x["op"] == "gen_ai.chat")
+    assert len(chat_spans) == 1
+    assert chat_spans[0]["origin"] == "auto.ai.langchain"
+
+    assert chat_spans[0]["data"]["gen_ai.system"] == "openai-chat"
+    assert chat_spans[0]["data"]["gen_ai.usage.input_tokens"] == 10
+    assert chat_spans[0]["data"]["gen_ai.usage.output_tokens"] == 20
+    assert chat_spans[0]["data"]["gen_ai.usage.total_tokens"] == 30
+
+    if send_default_pii and include_prompts:
+        assert (
+            chat_spans[0]["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
+            == "Hello, how can I help you?"
+        )
+
+        param_id = request.node.callspec.id
+        if "string" in param_id:
+            assert [
+                {
+                    "type": "text",
+                    "content": "You are very powerful assistant, but don't know current events",
+                }
+            ] == json.loads(chat_spans[0]["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS])
+        else:
+            assert [
+                {
+                    "type": "text",
+                    "content": "You are a helpful assistant.",
+                },
+                {
+                    "type": "text",
+                    "content": "Be concise and clear.",
+                },
+            ] == json.loads(chat_spans[0]["data"][SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS])
+    else:
+        assert SPANDATA.GEN_AI_SYSTEM_INSTRUCTIONS not in chat_spans[0].get("data", {})
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in chat_spans[0].get("data", {})
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in chat_spans[0].get("data", {})
+
+
+@pytest.mark.skipif(
+    LANGCHAIN_VERSION < (1,),
+    reason="LangChain 1.0+ required (ONE AGENT refactor)",
+)
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
+    ],
+)
+def test_tool_execution_span(
+    sentry_init,
+    capture_events,
+    send_default_pii,
+    include_prompts,
+    get_model_response,
+    responses_tool_call_model_responses,
+):
+    sentry_init(
+        integrations=[
+            LangchainIntegration(
+                include_prompts=include_prompts,
+            )
+        ],
+        traces_sample_rate=1.0,
+        send_default_pii=send_default_pii,
+    )
+    events = capture_events()
+
+    responses = responses_tool_call_model_responses(
+        tool_name="get_word_length",
+        arguments='{"word": "eudca"}',
+        response_model="gpt-4-0613",
+        response_text="The word eudca has 5 letters.",
+        response_ids=iter(["resp_1", "resp_2"]),
+        usages=iter(
+            [
+                ResponseUsage(
+                    input_tokens=142,
+                    input_tokens_details=InputTokensDetails(
+                        cached_tokens=0,
+                    ),
+                    output_tokens=50,
+                    output_tokens_details=OutputTokensDetails(
+                        reasoning_tokens=0,
+                    ),
+                    total_tokens=192,
+                ),
+                ResponseUsage(
+                    input_tokens=89,
+                    input_tokens_details=InputTokensDetails(
+                        cached_tokens=0,
+                    ),
+                    output_tokens=28,
+                    output_tokens_details=OutputTokensDetails(
+                        reasoning_tokens=0,
+                    ),
+                    total_tokens=117,
+                ),
+            ]
+        ),
+    )
+    tool_response = get_model_response(
+        next(responses),
+        serialize_pydantic=True,
+        request_headers={
+            "X-Stainless-Raw-Response": "True",
+        },
+    )
+    final_response = get_model_response(
+        next(responses),
+        serialize_pydantic=True,
+        request_headers={
+            "X-Stainless-Raw-Response": "True",
+        },
+    )
+
+    llm = ChatOpenAI(
+        model_name="gpt-4",
+        temperature=0,
+        openai_api_key="badkey",
+        use_responses_api=True,
+    )
+    agent = create_agent(
+        model=llm,
+        tools=[get_word_length],
+        name="word_length_agent",
+    )
+
+    with patch.object(
+        llm.client._client._client,
+        "send",
+        side_effect=[tool_response, final_response],
+    ) as _:
+        with start_transaction():
+            agent.invoke(
+                {
+                    "messages": [
+                        HumanMessage(content="How many letters in the word eudca"),
+                    ],
+                },
+            )
+
+    tx = events[0]
+    assert tx["type"] == "transaction"
+    assert tx["contexts"]["trace"]["origin"] == "manual"
+
+    chat_spans = list(x for x in tx["spans"] if x["op"] == "gen_ai.chat")
+    assert len(chat_spans) == 2
+
+    tool_exec_spans = list(x for x in tx["spans"] if x["op"] == "gen_ai.execute_tool")
+    assert len(tool_exec_spans) == 1
+    tool_exec_span = tool_exec_spans[0]
+
+    assert chat_spans[0]["origin"] == "auto.ai.langchain"
+    assert chat_spans[1]["origin"] == "auto.ai.langchain"
+    assert tool_exec_span["origin"] == "auto.ai.langchain"
+
+    assert chat_spans[0]["data"]["gen_ai.usage.input_tokens"] == 142
+    assert chat_spans[0]["data"]["gen_ai.usage.output_tokens"] == 50
+    assert chat_spans[0]["data"]["gen_ai.usage.total_tokens"] == 192
+    assert chat_spans[0]["data"]["gen_ai.system"] == "openai-chat"
+
+    assert chat_spans[1]["data"]["gen_ai.usage.input_tokens"] == 89
+    assert chat_spans[1]["data"]["gen_ai.usage.output_tokens"] == 28
+    assert chat_spans[1]["data"]["gen_ai.usage.total_tokens"] == 117
+    assert chat_spans[1]["data"]["gen_ai.system"] == "openai-chat"
+
+    if send_default_pii and include_prompts:
+        assert "word" in tool_exec_span["data"][SPANDATA.GEN_AI_TOOL_INPUT]
+
+        assert "5" in chat_spans[1]["data"][SPANDATA.GEN_AI_RESPONSE_TEXT]
+
+        # Verify tool calls are recorded when PII is enabled
+        assert SPANDATA.GEN_AI_RESPONSE_TOOL_CALLS in chat_spans[0].get("data", {}), (
+            "Tool calls should be recorded when send_default_pii=True and include_prompts=True"
+        )
+        tool_calls_data = chat_spans[0]["data"][SPANDATA.GEN_AI_RESPONSE_TOOL_CALLS]
+        assert isinstance(tool_calls_data, str)
+        assert "get_word_length" in tool_calls_data
+    else:
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in chat_spans[0].get("data", {})
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in chat_spans[0].get("data", {})
+        assert SPANDATA.GEN_AI_REQUEST_MESSAGES not in chat_spans[1].get("data", {})
+        assert SPANDATA.GEN_AI_RESPONSE_TEXT not in chat_spans[1].get("data", {})
+        assert SPANDATA.GEN_AI_TOOL_INPUT not in tool_exec_span.get("data", {})
+        assert SPANDATA.GEN_AI_TOOL_OUTPUT not in tool_exec_span.get("data", {})
+
+        # Verify tool calls are NOT recorded when PII is disabled
+        assert SPANDATA.GEN_AI_RESPONSE_TOOL_CALLS not in chat_spans[0].get(
+            "data", {}
+        ), (
+            f"Tool calls should NOT be recorded when send_default_pii={send_default_pii} "
+            f"and include_prompts={include_prompts}"
+        )
+        assert SPANDATA.GEN_AI_RESPONSE_TOOL_CALLS not in chat_spans[1].get(
+            "data", {}
+        ), (
+            f"Tool calls should NOT be recorded when send_default_pii={send_default_pii} "
+            f"and include_prompts={include_prompts}"
+        )
+
+    # Verify that available tools are always recorded regardless of PII settings
+    for chat_span in chat_spans:
+        tools_data = chat_span["data"][SPANDATA.GEN_AI_REQUEST_AVAILABLE_TOOLS]
+        assert "get_word_length" in tools_data
+
+
+@pytest.mark.parametrize(
+    "send_default_pii, include_prompts",
+    [
+        (True, True),
+        (True, False),
+        (False, True),
+        (False, False),
     ],
 )
 @pytest.mark.parametrize(
@@ -87,18 +484,16 @@ def _llm_type(self) -> str:
     ],
     ids=["string", "list", "blocks"],
 )
-def test_langchain_agent(
+def test_langchain_openai_tools_agent(
     sentry_init,
     capture_events,
     send_default_pii,
     include_prompts,
-    use_unknown_llm_type,
     system_instructions_content,
     request,
+    get_model_response,
+    server_side_event_chunks,
 ):
-    global llm_type
-    llm_type = "acme-llm" if use_unknown_llm_type else "openai-chat"
-
     sentry_init(
         integrations=[
             LangchainIntegration(
@@ -120,87 +515,173 @@ def test_langchain_agent(
             MessagesPlaceholder(variable_name="agent_scratchpad"),
         ]
     )
-    global stream_result_mock
-    stream_result_mock = Mock(
-        side_effect=[
+
+    tool_response = get_model_response(
+        server_side_event_chunks(
             [
-                ChatGenerationChunk(
-                    type="ChatGenerationChunk",
-                    message=AIMessageChunk(
-                        content="",
-                        additional_kwargs={
-                            "tool_calls": [
-                                {
-                                    "index": 0,
-                                    "id": "call_BbeyNhCKa6kYLYzrD40NGm3b",
-                                    "function": {
-                                        "arguments": "",
-                                        "name": "get_word_length",
-                                    },
-                                    "type": "function",
-                                }
-                            ]
-                        },
-                    ),
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-1",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[
+                        Choice(
+                            index=0,
+                            delta=ChoiceDelta(role="assistant"),
+                            finish_reason=None,
+                        ),
+                    ],
                 ),
-                ChatGenerationChunk(
-                    type="ChatGenerationChunk",
-                    message=AIMessageChunk(
-                        content="",
-                        additional_kwargs={
-                            "tool_calls": [
-                                {
-                                    "index": 0,
-                                    "id": None,
-                                    "function": {
-                                        "arguments": '{"word": "eudca"}',
-                                        "name": None,
-                                    },
-                                    "type": None,
-                                }
-                            ]
-                        },
-                    ),
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-1",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[
+                        Choice(
+                            index=0,
+                            delta=ChoiceDelta(
+                                tool_calls=[
+                                    ChoiceDeltaToolCall(
+                                        index=0,
+                                        id="call_BbeyNhCKa6kYLYzrD40NGm3b",
+                                        type="function",
+                                        function=ChoiceDeltaToolCallFunction(
+                                            name="get_word_length",
+                                            arguments="",
+                                        ),
+                                    ),
+                                ],
+                            ),
+                            finish_reason=None,
+                        ),
+                    ],
                 ),
-                ChatGenerationChunk(
-                    type="ChatGenerationChunk",
-                    message=AIMessageChunk(
-                        content="5",
-                        usage_metadata={
-                            "input_tokens": 142,
-                            "output_tokens": 50,
-                            "total_tokens": 192,
-                            "input_token_details": {"audio": 0, "cache_read": 0},
-                            "output_token_details": {"audio": 0, "reasoning": 0},
-                        },
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-1",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[
+                        Choice(
+                            index=0,
+                            delta=ChoiceDelta(
+                                tool_calls=[
+                                    ChoiceDeltaToolCall(
+                                        index=0,
+                                        function=ChoiceDeltaToolCallFunction(
+                                            arguments='{"word": "eudca"}',
+                                        ),
+                                    ),
+                                ],
+                            ),
+                            finish_reason=None,
+                        ),
+                    ],
+                ),
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-1",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[
+                        Choice(
+                            index=0,
+                            delta=ChoiceDelta(content="5"),
+                            finish_reason=None,
+                        ),
+                    ],
+                ),
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-1",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[
+                        Choice(
+                            index=0,
+                            delta=ChoiceDelta(),
+                            finish_reason="function_call",
+                        ),
+                    ],
+                ),
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-1",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[],
+                    usage=CompletionUsage(
+                        prompt_tokens=142,
+                        completion_tokens=50,
+                        total_tokens=192,
                     ),
-                    generation_info={"finish_reason": "function_call"},
                 ),
             ],
+            include_event_type=False,
+        )
+    )
+
+    final_response = get_model_response(
+        server_side_event_chunks(
             [
-                ChatGenerationChunk(
-                    text="The word eudca has 5 letters.",
-                    type="ChatGenerationChunk",
-                    message=AIMessageChunk(
-                        content="The word eudca has 5 letters.",
-                        usage_metadata={
-                            "input_tokens": 89,
-                            "output_tokens": 28,
-                            "total_tokens": 117,
-                            "input_token_details": {"audio": 0, "cache_read": 0},
-                            "output_token_details": {"audio": 0, "reasoning": 0},
-                        },
-                    ),
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-2",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[
+                        Choice(
+                            index=0,
+                            delta=ChoiceDelta(role="assistant"),
+                            finish_reason=None,
+                        ),
+                    ],
                 ),
-                ChatGenerationChunk(
-                    type="ChatGenerationChunk",
-                    generation_info={"finish_reason": "stop"},
-                    message=AIMessageChunk(content=""),
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-2",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[
+                        Choice(
+                            index=0,
+                            delta=ChoiceDelta(content="The word eudca has 5 letters."),
+                            finish_reason=None,
+                        ),
+                    ],
+                ),
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-2",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[
+                        Choice(
+                            index=0,
+                            delta=ChoiceDelta(),
+                            finish_reason="stop",
+                        ),
+                    ],
+                ),
+                ChatCompletionChunk(
+                    id="chatcmpl-turn-2",
+                    object="chat.completion.chunk",
+                    created=10000000,
+                    model="gpt-3.5-turbo",
+                    choices=[],
+                    usage=CompletionUsage(
+                        prompt_tokens=89,
+                        completion_tokens=28,
+                        total_tokens=117,
+                    ),
                 ),
             ],
-        ]
+            include_event_type=False,
+        )
     )
-    llm = MockOpenAI(
+
+    llm = ChatOpenAI(
         model_name="gpt-3.5-turbo",
         temperature=0,
         openai_api_key="badkey",
@@ -209,16 +690,29 @@ def test_langchain_agent(
 
     agent_executor = AgentExecutor(agent=agent, tools=[get_word_length], verbose=True)
 
-    with start_transaction():
-        list(agent_executor.stream({"input": "How many letters in the word eudca"}))
+    with patch.object(
+        llm.client._client._client,
+        "send",
+        side_effect=[tool_response, final_response],
+    ) as _:
+        with start_transaction():
+            list(agent_executor.stream({"input": "How many letters in the word eudca"}))
 
     tx = events[0]
     assert tx["type"] == "transaction"
+    assert tx["contexts"]["trace"]["origin"] == "manual"
+
+    invoke_agent_span = next(x for x in tx["spans"] if x["op"] == "gen_ai.invoke_agent")
     chat_spans = list(x for x in tx["spans"] if x["op"] == "gen_ai.chat")
     tool_exec_span = next(x for x in tx["spans"] if x["op"] == "gen_ai.execute_tool")
 
     assert len(chat_spans) == 2
 
+    assert invoke_agent_span["origin"] == "auto.ai.langchain"
+    assert chat_spans[0]["origin"] == "auto.ai.langchain"
+    assert chat_spans[1]["origin"] == "auto.ai.langchain"
+    assert tool_exec_span["origin"] == "auto.ai.langchain"
+
     # We can't guarantee anything about the "shape" of the langchain execution graph
     assert len(list(x for x in tx["spans"] if x["op"] == "gen_ai.chat")) > 0
 
@@ -297,17 +791,25 @@ def test_langchain_agent(
             f"and include_prompts={include_prompts}"
         )
 
+    # Verify finish_reasons is always an array of strings
+    assert chat_spans[0]["data"][SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS] == [
+        "function_call"
+    ]
+    assert chat_spans[1]["data"][SPANDATA.GEN_AI_RESPONSE_FINISH_REASONS] == ["stop"]
+
     # Verify that available tools are always recorded regardless of PII settings
     for chat_span in chat_spans:
-        span_data = chat_span.get("data", {})
-        if SPANDATA.GEN_AI_REQUEST_AVAILABLE_TOOLS in span_data:
-            tools_data = span_data[SPANDATA.GEN_AI_REQUEST_AVAILABLE_TOOLS]
-            assert tools_data is not None, (
-                "Available tools should always be recorded regardless of PII settings"
-            )
+        tools_data = chat_span["data"][SPANDATA.GEN_AI_REQUEST_AVAILABLE_TOOLS]
+        assert tools_data is not None, (
+            "Available tools should always be recorded regardless of PII settings"
+        )
+        assert "get_word_length" in tools_data
 
 
 def test_langchain_error(sentry_init, capture_events):
+    global llm_type
+    llm_type = "acme-llm"
+
     sentry_init(
         integrations=[LangchainIntegration(include_prompts=True)],
         traces_sample_rate=1.0,
@@ -387,122 +889,6 @@ def test_span_status_error(sentry_init, capture_events):
     assert transaction["contexts"]["trace"]["status"] == "internal_error"
 
 
-def test_span_origin(sentry_init, capture_events):
-    sentry_init(
-        integrations=[LangchainIntegration()],
-        traces_sample_rate=1.0,
-    )
-    events = capture_events()
-
-    prompt = ChatPromptTemplate.from_messages(
-        [
-            (
-                "system",
-                "You are very powerful assistant, but don't know current events",
-            ),
-            ("user", "{input}"),
-            MessagesPlaceholder(variable_name="agent_scratchpad"),
-        ]
-    )
-    global stream_result_mock
-    stream_result_mock = Mock(
-        side_effect=[
-            [
-                ChatGenerationChunk(
-                    type="ChatGenerationChunk",
-                    message=AIMessageChunk(
-                        content="",
-                        additional_kwargs={
-                            "tool_calls": [
-                                {
-                                    "index": 0,
-                                    "id": "call_BbeyNhCKa6kYLYzrD40NGm3b",
-                                    "function": {
-                                        "arguments": "",
-                                        "name": "get_word_length",
-                                    },
-                                    "type": "function",
-                                }
-                            ]
-                        },
-                    ),
-                ),
-                ChatGenerationChunk(
-                    type="ChatGenerationChunk",
-                    message=AIMessageChunk(
-                        content="",
-                        additional_kwargs={
-                            "tool_calls": [
-                                {
-                                    "index": 0,
-                                    "id": None,
-                                    "function": {
-                                        "arguments": '{"word": "eudca"}',
-                                        "name": None,
-                                    },
-                                    "type": None,
-                                }
-                            ]
-                        },
-                    ),
-                ),
-                ChatGenerationChunk(
-                    type="ChatGenerationChunk",
-                    message=AIMessageChunk(
-                        content="5",
-                        usage_metadata={
-                            "input_tokens": 142,
-                            "output_tokens": 50,
-                            "total_tokens": 192,
-                            "input_token_details": {"audio": 0, "cache_read": 0},
-                            "output_token_details": {"audio": 0, "reasoning": 0},
-                        },
-                    ),
-                    generation_info={"finish_reason": "function_call"},
-                ),
-            ],
-            [
-                ChatGenerationChunk(
-                    text="The word eudca has 5 letters.",
-                    type="ChatGenerationChunk",
-                    message=AIMessageChunk(
-                        content="The word eudca has 5 letters.",
-                        usage_metadata={
-                            "input_tokens": 89,
-                            "output_tokens": 28,
-                            "total_tokens": 117,
-                            "input_token_details": {"audio": 0, "cache_read": 0},
-                            "output_token_details": {"audio": 0, "reasoning": 0},
-                        },
-                    ),
-                ),
-                ChatGenerationChunk(
-                    type="ChatGenerationChunk",
-                    generation_info={"finish_reason": "stop"},
-                    message=AIMessageChunk(content=""),
-                ),
-            ],
-        ]
-    )
-    llm = MockOpenAI(
-        model_name="gpt-3.5-turbo",
-        temperature=0,
-        openai_api_key="badkey",
-    )
-    agent = create_openai_tools_agent(llm, [get_word_length], prompt)
-
-    agent_executor = AgentExecutor(agent=agent, tools=[get_word_length], verbose=True)
-
-    with start_transaction():
-        list(agent_executor.stream({"input": "How many letters in the word eudca"}))
-
-    (event,) = events
-
-    assert event["contexts"]["trace"]["origin"] == "manual"
-    for span in event["spans"]:
-        assert span["origin"] == "auto.ai.langchain"
-
-
 def test_manual_callback_no_duplication(sentry_init):
     """
     Test that when a user manually provides a SentryLangchainCallback,
@@ -712,155 +1098,6 @@ def test_langchain_callback_list_existing_callback(sentry_init):
         assert handler is sentry_callback
 
 
-def test_tools_integration_in_spans(sentry_init, capture_events):
-    """Test that tools are properly set on spans in actual LangChain integration."""
-    global llm_type
-    llm_type = "openai-chat"
-
-    sentry_init(
-        integrations=[LangchainIntegration(include_prompts=False)],
-        traces_sample_rate=1.0,
-    )
-    events = capture_events()
-
-    prompt = ChatPromptTemplate.from_messages(
-        [
-            ("system", "You are a helpful assistant"),
-            ("user", "{input}"),
-            MessagesPlaceholder(variable_name="agent_scratchpad"),
-        ]
-    )
-
-    global stream_result_mock
-    stream_result_mock = Mock(
-        side_effect=[
-            [
-                ChatGenerationChunk(
-                    type="ChatGenerationChunk",
-                    message=AIMessageChunk(content="Simple response"),
-                ),
-            ]
-        ]
-    )
-
-    llm = MockOpenAI(
-        model_name="gpt-3.5-turbo",
-        temperature=0,
-        openai_api_key="badkey",
-    )
-    agent = create_openai_tools_agent(llm, [get_word_length], prompt)
-    agent_executor = AgentExecutor(agent=agent, tools=[get_word_length], verbose=True)
-
-    with start_transaction():
-        list(agent_executor.stream({"input": "Hello"}))
-
-    # Check that events were captured and contain tools data
-    if events:
-        tx = events[0]
-        spans = tx.get("spans", [])
-
-        # Look for spans that should have tools data
-        tools_found = False
-        for span in spans:
-            span_data = span.get("data", {})
-            if SPANDATA.GEN_AI_REQUEST_AVAILABLE_TOOLS in span_data:
-                tools_found = True
-                tools_data = span_data[SPANDATA.GEN_AI_REQUEST_AVAILABLE_TOOLS]
-                # Verify tools are in the expected format
-                assert isinstance(tools_data, (str, list))  # Could be serialized
-                if isinstance(tools_data, str):
-                    # If serialized as string, should contain tool name
-                    assert "get_word_length" in tools_data
-                else:
-                    # If still a list, verify structure
-                    assert len(tools_data) >= 1
-                    names = [
-                        tool.get("name")
-                        for tool in tools_data
-                        if isinstance(tool, dict)
-                    ]
-                    assert "get_word_length" in names
-
-        # Ensure we found at least one span with tools data
-        assert tools_found, "No spans found with tools data"
-
-
-def test_langchain_integration_with_langchain_core_only(sentry_init, capture_events):
-    """Test that the langchain integration works when langchain.agents.AgentExecutor
-    is not available or langchain is not installed, but langchain-core is.
-    """
-
-    from langchain_core.outputs import LLMResult, Generation
-
-    with patch("sentry_sdk.integrations.langchain.AgentExecutor", None):
-        from sentry_sdk.integrations.langchain import (
-            LangchainIntegration,
-            SentryLangchainCallback,
-        )
-
-        sentry_init(
-            integrations=[LangchainIntegration(include_prompts=True)],
-            traces_sample_rate=1.0,
-            send_default_pii=True,
-        )
-        events = capture_events()
-
-        try:
-            LangchainIntegration.setup_once()
-        except Exception as e:
-            pytest.fail(f"setup_once() failed when AgentExecutor is None: {e}")
-
-        callback = SentryLangchainCallback(max_span_map_size=100, include_prompts=True)
-
-        run_id = "12345678-1234-1234-1234-123456789012"
-        serialized = {"_type": "openai-chat", "model_name": "gpt-3.5-turbo"}
-        prompts = ["What is the capital of France?"]
-
-        with start_transaction():
-            callback.on_llm_start(
-                serialized=serialized,
-                prompts=prompts,
-                run_id=run_id,
-                invocation_params={
-                    "temperature": 0.7,
-                    "max_tokens": 100,
-                    "model": "gpt-3.5-turbo",
-                },
-            )
-
-            response = LLMResult(
-                generations=[[Generation(text="The capital of France is Paris.")]],
-                llm_output={
-                    "token_usage": {
-                        "total_tokens": 25,
-                        "prompt_tokens": 10,
-                        "completion_tokens": 15,
-                    }
-                },
-            )
-            callback.on_llm_end(response=response, run_id=run_id)
-
-        assert len(events) > 0
-        tx = events[0]
-        assert tx["type"] == "transaction"
-
-        llm_spans = [
-            span for span in tx.get("spans", []) if span.get("op") == "gen_ai.pipeline"
-        ]
-        assert len(llm_spans) > 0
-
-        llm_span = llm_spans[0]
-        assert llm_span["description"] == "Langchain LLM call"
-        assert llm_span["data"]["gen_ai.request.model"] == "gpt-3.5-turbo"
-        assert (
-            llm_span["data"]["gen_ai.response.text"]
-            == "The capital of France is Paris."
-        )
-        assert llm_span["data"]["gen_ai.usage.total_tokens"] == 25
-        assert llm_span["data"]["gen_ai.usage.input_tokens"] == 10
-        assert llm_span["data"]["gen_ai.usage.output_tokens"] == 15
-
-
 def test_langchain_message_role_mapping(sentry_init, capture_events):
     """Test that message roles are properly normalized in langchain integration."""
     global llm_type
@@ -1032,6 +1269,7 @@ def test_langchain_message_truncation(sentry_init, capture_events):
             serialized=serialized,
             prompts=prompts,
             run_id=run_id,
+            name="my_pipeline",
             invocation_params={
                 "temperature": 0.7,
                 "max_tokens": 100,
@@ -1056,13 +1294,15 @@ def test_langchain_message_truncation(sentry_init, capture_events):
     assert tx["type"] == "transaction"
 
     llm_spans = [
-        span for span in tx.get("spans", []) if span.get("op") == "gen_ai.pipeline"
+        span for span in tx.get("spans", []) if span.get("op") == "gen_ai.generate_text"
     ]
     assert len(llm_spans) > 0
 
     llm_span = llm_spans[0]
-    assert SPANDATA.GEN_AI_REQUEST_MESSAGES in llm_span["data"]
+    assert llm_span["data"]["gen_ai.operation.name"] == "generate_text"
+    assert llm_span["data"][SPANDATA.GEN_AI_PIPELINE_NAME] == "my_pipeline"
 
+    assert SPANDATA.GEN_AI_REQUEST_MESSAGES in llm_span["data"]
     messages_data = llm_span["data"][SPANDATA.GEN_AI_REQUEST_MESSAGES]
     assert isinstance(messages_data, str)
 
@@ -1770,11 +2010,12 @@ def test_langchain_response_model_extraction(
     assert tx["type"] == "transaction"
 
     llm_spans = [
-        span for span in tx.get("spans", []) if span.get("op") == "gen_ai.pipeline"
+        span for span in tx.get("spans", []) if span.get("op") == "gen_ai.generate_text"
     ]
     assert len(llm_spans) > 0
 
     llm_span = llm_spans[0]
+    assert llm_span["data"]["gen_ai.operation.name"] == "generate_text"
 
     if expected_model is not None:
         assert SPANDATA.GEN_AI_RESPONSE_MODEL in llm_span["data"]
@@ -1994,6 +2235,94 @@ def test_transform_google_file_data(self):
         }
 
 
+@pytest.mark.parametrize(
+    "ai_type,expected_system",
+    [
+        # Real LangChain _type values (from _llm_type properties)
+        # OpenAI
+        ("openai-chat", "openai-chat"),
+        ("openai", "openai"),
+        # Azure OpenAI
+        ("azure-openai-chat", "azure-openai-chat"),
+        ("azure", "azure"),
+        # Anthropic
+        ("anthropic-chat", "anthropic-chat"),
+        # Google
+        ("vertexai", "vertexai"),
+        ("chat-google-generative-ai", "chat-google-generative-ai"),
+        ("google_gemini", "google_gemini"),
+        # AWS Bedrock
+        ("amazon_bedrock_chat", "amazon_bedrock_chat"),
+        ("amazon_bedrock", "amazon_bedrock"),
+        # Cohere
+        ("cohere-chat", "cohere-chat"),
+        # Ollama
+        ("chat-ollama", "chat-ollama"),
+        ("ollama-llm", "ollama-llm"),
+        # Mistral
+        ("mistralai-chat", "mistralai-chat"),
+        # Fireworks
+        ("fireworks-chat", "fireworks-chat"),
+        ("fireworks", "fireworks"),
+        # HuggingFace
+        ("huggingface-chat-wrapper", "huggingface-chat-wrapper"),
+        # Groq
+        ("groq-chat", "groq-chat"),
+        # NVIDIA
+        ("chat-nvidia-ai-playground", "chat-nvidia-ai-playground"),
+        # xAI
+        ("xai-chat", "xai-chat"),
+        # DeepSeek
+        ("chat-deepseek", "chat-deepseek"),
+        # Edge cases
+        ("", None),
+        (None, None),
+    ],
+)
+def test_langchain_ai_system_detection(
+    sentry_init, capture_events, ai_type, expected_system
+):
+    sentry_init(
+        integrations=[LangchainIntegration()],
+        traces_sample_rate=1.0,
+    )
+    events = capture_events()
+
+    callback = SentryLangchainCallback(max_span_map_size=100, include_prompts=True)
+
+    run_id = "test-ai-system-uuid"
+    serialized = {"_type": ai_type} if ai_type is not None else {}
+    prompts = ["Test prompt"]
+
+    with start_transaction():
+        callback.on_llm_start(
+            serialized=serialized,
+            prompts=prompts,
+            run_id=run_id,
+            invocation_params={"_type": ai_type, "model": "test-model"},
+        )
+
+        generation = Mock(text="Test response", message=None)
+        response = Mock(generations=[[generation]])
+        callback.on_llm_end(response=response, run_id=run_id)
+
+    assert len(events) > 0
+    tx = events[0]
+    assert tx["type"] == "transaction"
+
+    llm_spans = [
+        span for span in tx.get("spans", []) if span.get("op") == "gen_ai.generate_text"
+    ]
+    assert len(llm_spans) > 0
+
+    llm_span = llm_spans[0]
+
+    if expected_system is not None:
+        assert llm_span["data"][SPANDATA.GEN_AI_SYSTEM] == expected_system
+    else:
+        assert SPANDATA.GEN_AI_SYSTEM not in llm_span.get("data", {})
+
+
 class TestTransformLangchainMessageContent:
     """Tests for _transform_langchain_message_content function."""
 
diff --git a/tests/integrations/litellm/test_litellm.py b/tests/integrations/litellm/test_litellm.py
index ef129c6cfd..9022093fa3 100644
--- a/tests/integrations/litellm/test_litellm.py
+++ b/tests/integrations/litellm/test_litellm.py
@@ -19,7 +19,6 @@ async def __call__(self, *args, **kwargs):
 except ImportError:
     pytest.skip("litellm not installed", allow_module_level=True)
 
-import sentry_sdk
 from sentry_sdk import start_transaction
 from sentry_sdk.consts import OP, SPANDATA
 from sentry_sdk._types import BLOB_DATA_SUBSTITUTE
diff --git a/tests/integrations/logging/test_logging.py b/tests/integrations/logging/test_logging.py
index 7b144f4b55..5e384bd3db 100644
--- a/tests/integrations/logging/test_logging.py
+++ b/tests/integrations/logging/test_logging.py
@@ -5,7 +5,13 @@
 
 from sentry_sdk import get_client
 from sentry_sdk.consts import VERSION
-from sentry_sdk.integrations.logging import LoggingIntegration, ignore_logger
+from sentry_sdk.integrations.logging import (
+    LoggingIntegration,
+    ignore_logger,
+    ignore_logger_for_sentry_logs,
+    unignore_logger,
+    unignore_logger_for_sentry_logs,
+)
 from tests.test_logs import envelopes_to_logs
 
 other_logger = logging.getLogger("testfoo")
@@ -222,34 +228,37 @@ def test_logging_captured_warnings(sentry_init, capture_events, recwarn):
     assert str(recwarn[0].message) == "third"
 
 
-def test_ignore_logger(sentry_init, capture_events):
+def test_ignore_logger(sentry_init, capture_events, request):
     sentry_init(integrations=[LoggingIntegration()], default_integrations=False)
     events = capture_events()
 
     ignore_logger("testfoo")
+    request.addfinalizer(lambda: unignore_logger("testfoo"))
 
     other_logger.error("hi")
 
     assert not events
 
 
-def test_ignore_logger_whitespace_padding(sentry_init, capture_events):
+def test_ignore_logger_whitespace_padding(sentry_init, capture_events, request):
     """Here we test insensitivity to whitespace padding of ignored loggers"""
     sentry_init(integrations=[LoggingIntegration()], default_integrations=False)
     events = capture_events()
 
     ignore_logger("testfoo")
+    request.addfinalizer(lambda: unignore_logger("testfoo"))
 
     padded_logger = logging.getLogger("       testfoo   ")
     padded_logger.error("hi")
     assert not events
 
 
-def test_ignore_logger_wildcard(sentry_init, capture_events):
+def test_ignore_logger_wildcard(sentry_init, capture_events, request):
     sentry_init(integrations=[LoggingIntegration()], default_integrations=False)
     events = capture_events()
 
     ignore_logger("testfoo.*")
+    request.addfinalizer(lambda: unignore_logger("testfoo.*"))
 
     nested_logger = logging.getLogger("testfoo.submodule")
 
@@ -262,6 +271,44 @@ def test_ignore_logger_wildcard(sentry_init, capture_events):
     assert event["logentry"]["formatted"] == "hi"
 
 
+def test_ignore_logger_does_not_affect_sentry_logs(
+    sentry_init, capture_envelopes, request
+):
+    """ignore_logger should suppress events/breadcrumbs but not Sentry Logs."""
+    sentry_init(enable_logs=True)
+    envelopes = capture_envelopes()
+
+    ignore_logger("testfoo")
+    request.addfinalizer(lambda: unignore_logger("testfoo"))
+
+    other_logger.error("hi")
+    get_client().flush()
+
+    logs = envelopes_to_logs(envelopes)
+    assert len(logs) == 1
+    assert logs[0]["body"] == "hi"
+
+
+def test_ignore_logger_for_sentry_logs(sentry_init, capture_envelopes, request):
+    """ignore_logger_for_sentry_logs should suppress Sentry Logs but not events."""
+    sentry_init(enable_logs=True)
+    envelopes = capture_envelopes()
+
+    ignore_logger_for_sentry_logs("testfoo")
+    request.addfinalizer(lambda: unignore_logger_for_sentry_logs("testfoo"))
+
+    other_logger.error("hi")
+    get_client().flush()
+
+    # Event should still be captured
+    event_envelopes = [e for e in envelopes if e.items[0].type == "event"]
+    assert len(event_envelopes) == 1
+
+    # But no Sentry Logs
+    logs = envelopes_to_logs(envelopes)
+    assert len(logs) == 0
+
+
 def test_logging_dictionary_interpolation(sentry_init, capture_events):
     """Here we test an entire dictionary being interpolated into the log message."""
     sentry_init(integrations=[LoggingIntegration()], default_integrations=False)
diff --git a/tests/integrations/openai/test_openai.py b/tests/integrations/openai/test_openai.py
index 7f75bb977e..23fb0d9ad7 100644
--- a/tests/integrations/openai/test_openai.py
+++ b/tests/integrations/openai/test_openai.py
@@ -46,8 +46,6 @@
     OpenAIIntegration,
     _calculate_token_usage,
 )
-from sentry_sdk._types import AnnotatedValue
-from sentry_sdk.serializer import serialize
 from sentry_sdk.utils import safe_serialize
 
 from unittest import mock  # python 3.3 and above
diff --git a/tests/integrations/openai_agents/test_openai_agents.py b/tests/integrations/openai_agents/test_openai_agents.py
index 117755b963..c428a822d4 100644
--- a/tests/integrations/openai_agents/test_openai_agents.py
+++ b/tests/integrations/openai_agents/test_openai_agents.py
@@ -1,5 +1,4 @@
 import asyncio
-import re
 import pytest
 from unittest.mock import MagicMock, patch
 import os
@@ -19,7 +18,6 @@
 from agents.models.openai_responses import OpenAIResponsesModel
 
 from unittest import mock
-from unittest.mock import AsyncMock
 
 import agents
 from agents import (
@@ -46,15 +44,12 @@
     ResponseCompletedEvent,
     Response,
     ResponseUsage,
-    ResponseStreamEvent,
 )
 from openai.types.responses.response_usage import (
     InputTokensDetails,
     OutputTokensDetails,
 )
 
-from openai._response import AsyncAPIResponse
-from openai._models import FinalRequestOptions
 
 test_run_config = agents.RunConfig(tracing_disabled=True)
 
@@ -107,45 +102,6 @@ def mock_usage():
     )
 
 
-@pytest.fixture
-def mock_model_response():
-    return Response(
-        id="resp_123",
-        output=[
-            ResponseOutputMessage(
-                id="msg_123",
-                type="message",
-                status="completed",
-                content=[
-                    ResponseOutputText(
-                        text="Hello, how can I help you?",
-                        type="output_text",
-                        annotations=[],
-                    )
-                ],
-                role="assistant",
-            )
-        ],
-        parallel_tool_calls=False,
-        tool_choice="none",
-        tools=[],
-        created_at=10000000,
-        model="gpt-4",
-        object="response",
-        usage=ResponseUsage(
-            input_tokens=10,
-            input_tokens_details=InputTokensDetails(
-                cached_tokens=0,
-            ),
-            output_tokens=20,
-            output_tokens_details=OutputTokensDetails(
-                reasoning_tokens=5,
-            ),
-            total_tokens=30,
-        ),
-    )
-
-
 @pytest.fixture
 def test_agent():
     """Create a real Agent instance for testing."""
@@ -201,34 +157,21 @@ def test_agent_custom_model():
     )
 
 
-@pytest.fixture
-def get_model_response():
-    def inner(response_content):
-        model_request = httpx.Request(
-            "POST",
-            "/responses",
-        )
-
-        response = httpx.Response(
-            200,
-            request=model_request,
-            content=json.dumps(response_content.model_dump()).encode("utf-8"),
-        )
-
-        return response
-
-    return inner
-
-
 @pytest.mark.asyncio
 async def test_agent_invocation_span_no_pii(
-    sentry_init, capture_events, test_agent, mock_model_response, get_model_response
+    sentry_init,
+    capture_events,
+    test_agent,
+    nonstreaming_responses_model_response,
+    get_model_response,
 ):
     client = AsyncOpenAI(api_key="test-key")
     model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
     agent = test_agent.clone(model=model)
 
-    response = get_model_response(mock_model_response)
+    response = get_model_response(
+        nonstreaming_responses_model_response, serialize_pydantic=True
+    )
 
     with patch.object(
         agent.model._client._client,
@@ -364,7 +307,7 @@ async def test_agent_invocation_span(
     sentry_init,
     capture_events,
     test_agent_with_instructions,
-    mock_model_response,
+    nonstreaming_responses_model_response,
     instructions,
     input,
     request,
@@ -377,7 +320,9 @@ async def test_agent_invocation_span(
     model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
     agent = test_agent_with_instructions(instructions).clone(model=model)
 
-    response = get_model_response(mock_model_response)
+    response = get_model_response(
+        nonstreaming_responses_model_response, serialize_pydantic=True
+    )
 
     with patch.object(
         agent.model._client._client,
@@ -527,7 +472,7 @@ async def test_client_span_custom_model(
     sentry_init,
     capture_events,
     test_agent_custom_model,
-    mock_model_response,
+    nonstreaming_responses_model_response,
     get_model_response,
 ):
     """
@@ -538,7 +483,9 @@ async def test_client_span_custom_model(
     model = OpenAIResponsesModel(model="my-custom-model", openai_client=client)
     agent = test_agent_custom_model.clone(model=model)
 
-    response = get_model_response(mock_model_response)
+    response = get_model_response(
+        nonstreaming_responses_model_response, serialize_pydantic=True
+    )
 
     with patch.object(
         agent.model._client._client,
@@ -571,7 +518,7 @@ def test_agent_invocation_span_sync_no_pii(
     sentry_init,
     capture_events,
     test_agent,
-    mock_model_response,
+    nonstreaming_responses_model_response,
     get_model_response,
 ):
     """
@@ -581,7 +528,9 @@ def test_agent_invocation_span_sync_no_pii(
     model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
     agent = test_agent.clone(model=model)
 
-    response = get_model_response(mock_model_response)
+    response = get_model_response(
+        nonstreaming_responses_model_response, serialize_pydantic=True
+    )
 
     with patch.object(
         agent.model._client._client,
@@ -711,7 +660,7 @@ def test_agent_invocation_span_sync(
     sentry_init,
     capture_events,
     test_agent_with_instructions,
-    mock_model_response,
+    nonstreaming_responses_model_response,
     instructions,
     input,
     request,
@@ -724,7 +673,9 @@ def test_agent_invocation_span_sync(
     model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
     agent = test_agent_with_instructions(instructions).clone(model=model)
 
-    response = get_model_response(mock_model_response)
+    response = get_model_response(
+        nonstreaming_responses_model_response, serialize_pydantic=True
+    )
 
     with patch.object(
         agent.model._client._client,
@@ -906,7 +857,8 @@ async def test_handoff_span(sentry_init, capture_events, get_model_response):
                 ),
                 total_tokens=30,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     final_response = get_model_response(
@@ -944,7 +896,8 @@ async def test_handoff_span(sentry_init, capture_events, get_model_response):
                 ),
                 total_tokens=30,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -1032,7 +985,8 @@ async def test_max_turns_before_handoff_span(
                 ),
                 total_tokens=30,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     final_response = get_model_response(
@@ -1070,7 +1024,8 @@ async def test_max_turns_before_handoff_span(
                 ),
                 total_tokens=30,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -1107,7 +1062,11 @@ async def test_max_turns_before_handoff_span(
 
 @pytest.mark.asyncio
 async def test_tool_execution_span(
-    sentry_init, capture_events, test_agent, get_model_response
+    sentry_init,
+    capture_events,
+    test_agent,
+    get_model_response,
+    responses_tool_call_model_responses,
 ):
     """
     Test tool execution span creation.
@@ -1123,74 +1082,46 @@ def simple_test_tool(message: str) -> str:
     model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
     agent_with_tool = test_agent.clone(tools=[simple_test_tool], model=model)
 
-    tool_response = get_model_response(
-        Response(
-            id="resp_tool_123",
-            output=[
-                ResponseFunctionToolCall(
-                    id="call_123",
-                    call_id="call_123",
-                    name="simple_test_tool",
-                    type="function_call",
-                    arguments='{"message": "hello"}',
-                )
-            ],
-            parallel_tool_calls=False,
-            tool_choice="none",
-            tools=[],
-            created_at=10000000,
-            model="gpt-4",
-            object="response",
-            usage=ResponseUsage(
-                input_tokens=10,
-                input_tokens_details=InputTokensDetails(
-                    cached_tokens=0,
+    responses = responses_tool_call_model_responses(
+        tool_name="simple_test_tool",
+        arguments='{"message": "hello"}',
+        response_model="gpt-4",
+        response_text="Task completed using the tool",
+        response_ids=iter(["resp_tool_123", "resp_final_123"]),
+        usages=iter(
+            [
+                ResponseUsage(
+                    input_tokens=10,
+                    input_tokens_details=InputTokensDetails(
+                        cached_tokens=0,
+                    ),
+                    output_tokens=5,
+                    output_tokens_details=OutputTokensDetails(
+                        reasoning_tokens=0,
+                    ),
+                    total_tokens=15,
                 ),
-                output_tokens=5,
-                output_tokens_details=OutputTokensDetails(
-                    reasoning_tokens=0,
+                ResponseUsage(
+                    input_tokens=15,
+                    input_tokens_details=InputTokensDetails(
+                        cached_tokens=0,
+                    ),
+                    output_tokens=10,
+                    output_tokens_details=OutputTokensDetails(
+                        reasoning_tokens=0,
+                    ),
+                    total_tokens=25,
                 ),
-                total_tokens=15,
-            ),
-        )
+            ]
+        ),
+    )
+    tool_response = get_model_response(
+        next(responses),
+        serialize_pydantic=True,
     )
-
     final_response = get_model_response(
-        Response(
-            id="resp_final_123",
-            output=[
-                ResponseOutputMessage(
-                    id="msg_final",
-                    type="message",
-                    status="completed",
-                    content=[
-                        ResponseOutputText(
-                            text="Task completed using the tool",
-                            type="output_text",
-                            annotations=[],
-                        )
-                    ],
-                    role="assistant",
-                )
-            ],
-            parallel_tool_calls=False,
-            tool_choice="none",
-            tools=[],
-            created_at=10000000,
-            model="gpt-4",
-            object="response",
-            usage=ResponseUsage(
-                input_tokens=15,
-                input_tokens_details=InputTokensDetails(
-                    cached_tokens=0,
-                ),
-                output_tokens=10,
-                output_tokens_details=OutputTokensDetails(
-                    reasoning_tokens=0,
-                ),
-                total_tokens=25,
-            ),
-        )
+        next(responses),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -1386,16 +1317,13 @@ def simple_test_tool(message: str) -> str:
     assert ai_client_span2["data"]["gen_ai.usage.total_tokens"] == 25
 
 
-def server_side_event_chunks(events):
-    for event in events:
-        payload = event.model_dump()
-        chunk = f"event: {payload['type']}\ndata: {json.dumps(payload)}\n\n"
-        yield chunk.encode("utf-8")
-
-
 @pytest.mark.asyncio
 async def test_hosted_mcp_tool_propagation_header_streamed(
-    sentry_init, test_agent, async_iterator
+    sentry_init,
+    test_agent,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
 ):
     """
     Test responses API is given trace propagation headers with HostedMCPTool.
@@ -1427,11 +1355,7 @@ async def test_hosted_mcp_tool_propagation_header_streamed(
         release="d08ebdb9309e1b004c6f52202de58a09c2268e42",
     )
 
-    request = httpx.Request(
-        "POST",
-        "/responses",
-    )
-
+    request_headers = {}
     # openai-agents calls with_streaming_response() if available starting with
     # https://github.com/openai/openai-agents-python/commit/159beb56130f7d85192acfd593c9168757984dc0.
     # When using with_streaming_response() the header set below changes the response type:
@@ -1439,12 +1363,10 @@ async def test_hosted_mcp_tool_propagation_header_streamed(
     if parse_version(OPENAI_AGENTS_VERSION) >= (0, 10, 3) and hasattr(
         agent_with_tool.model._client.responses, "with_streaming_response"
     ):
-        request.headers["X-Stainless-Raw-Response"] = "stream"
+        request_headers["X-Stainless-Raw-Response"] = "stream"
 
-    response = httpx.Response(
-        200,
-        request=request,
-        content=async_iterator(
+    response = get_model_response(
+        async_iterator(
             server_side_event_chunks(
                 [
                     ResponseCreatedEvent(
@@ -1503,6 +1425,7 @@ async def test_hosted_mcp_tool_propagation_header_streamed(
                 ]
             )
         ),
+        request_headers=request_headers,
     )
 
     # Patching https://github.com/openai/openai-python/blob/656e3cab4a18262a49b961d41293367e45ee71b9/src/openai/_base_client.py#L1604
@@ -1594,7 +1517,7 @@ async def test_hosted_mcp_tool_propagation_headers(
         release="d08ebdb9309e1b004c6f52202de58a09c2268e42",
     )
 
-    response = get_model_response(EXAMPLE_RESPONSE)
+    response = get_model_response(EXAMPLE_RESPONSE, serialize_pydantic=True)
 
     with patch.object(
         agent_with_tool.model._client._client,
@@ -1905,7 +1828,8 @@ async def test_mcp_tool_execution_spans(
                 ),
                 total_tokens=15,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     final_response = get_model_response(
@@ -1943,7 +1867,8 @@ async def test_mcp_tool_execution_spans(
                 ),
                 total_tokens=25,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -2035,7 +1960,8 @@ async def test_mcp_tool_execution_with_error(
                 ),
                 total_tokens=15,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     final_response = get_model_response(
@@ -2073,7 +1999,8 @@ async def test_mcp_tool_execution_with_error(
                 ),
                 total_tokens=25,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -2163,7 +2090,8 @@ async def test_mcp_tool_execution_without_pii(
                 ),
                 total_tokens=15,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     final_response = get_model_response(
@@ -2201,7 +2129,8 @@ async def test_mcp_tool_execution_without_pii(
                 ),
                 total_tokens=25,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -2249,7 +2178,11 @@ async def test_mcp_tool_execution_without_pii(
 
 @pytest.mark.asyncio
 async def test_multiple_agents_asyncio(
-    sentry_init, capture_events, test_agent, mock_model_response, get_model_response
+    sentry_init,
+    capture_events,
+    test_agent,
+    nonstreaming_responses_model_response,
+    get_model_response,
 ):
     """
     Test that multiple agents can be run at the same time in asyncio tasks
@@ -2259,7 +2192,9 @@ async def test_multiple_agents_asyncio(
     model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
     agent = test_agent.clone(model=model)
 
-    response = get_model_response(mock_model_response)
+    response = get_model_response(
+        nonstreaming_responses_model_response, serialize_pydantic=True
+    )
 
     with patch.object(
         agent.model._client._client,
@@ -2337,7 +2272,11 @@ def test_openai_agents_message_role_mapping(
 
 @pytest.mark.asyncio
 async def test_tool_execution_error_tracing(
-    sentry_init, capture_events, test_agent, get_model_response
+    sentry_init,
+    capture_events,
+    test_agent,
+    get_model_response,
+    responses_tool_call_model_responses,
 ):
     """
     Test that tool execution errors are properly tracked via error tracing patch.
@@ -2360,74 +2299,46 @@ def failing_tool(message: str) -> str:
     model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
     agent_with_tool = test_agent.clone(tools=[failing_tool], model=model)
 
-    tool_response = get_model_response(
-        Response(
-            id="resp_1",
-            output=[
-                ResponseFunctionToolCall(
-                    id="call_123",
-                    call_id="call_123",
-                    name="failing_tool",
-                    type="function_call",
-                    arguments='{"message": "test"}',
-                )
-            ],
-            parallel_tool_calls=False,
-            tool_choice="none",
-            tools=[],
-            created_at=10000000,
-            model="gpt-4.1-2025-04-14",
-            object="response",
-            usage=ResponseUsage(
-                input_tokens=10,
-                input_tokens_details=InputTokensDetails(
-                    cached_tokens=0,
+    responses = responses_tool_call_model_responses(
+        tool_name="failing_tool",
+        arguments='{"message": "test"}',
+        response_model="gpt-4-0613",
+        response_text="An error occurred while running the tool",
+        response_ids=iter(["resp_1", "resp_2"]),
+        usages=iter(
+            [
+                ResponseUsage(
+                    input_tokens=10,
+                    input_tokens_details=InputTokensDetails(
+                        cached_tokens=0,
+                    ),
+                    output_tokens=5,
+                    output_tokens_details=OutputTokensDetails(
+                        reasoning_tokens=0,
+                    ),
+                    total_tokens=15,
                 ),
-                output_tokens=5,
-                output_tokens_details=OutputTokensDetails(
-                    reasoning_tokens=0,
+                ResponseUsage(
+                    input_tokens=15,
+                    input_tokens_details=InputTokensDetails(
+                        cached_tokens=0,
+                    ),
+                    output_tokens=10,
+                    output_tokens_details=OutputTokensDetails(
+                        reasoning_tokens=0,
+                    ),
+                    total_tokens=25,
                 ),
-                total_tokens=15,
-            ),
-        )
+            ]
+        ),
+    )
+    tool_response = get_model_response(
+        next(responses),
+        serialize_pydantic=True,
     )
-
     final_response = get_model_response(
-        Response(
-            id="resp_2",
-            output=[
-                ResponseOutputMessage(
-                    id="msg_final",
-                    type="message",
-                    status="completed",
-                    content=[
-                        ResponseOutputText(
-                            text="An error occurred while running the tool",
-                            type="output_text",
-                            annotations=[],
-                        )
-                    ],
-                    role="assistant",
-                )
-            ],
-            parallel_tool_calls=False,
-            tool_choice="none",
-            tools=[],
-            created_at=10000000,
-            model="gpt-4-0613",
-            object="response",
-            usage=ResponseUsage(
-                input_tokens=15,
-                input_tokens_details=InputTokensDetails(
-                    cached_tokens=0,
-                ),
-                output_tokens=10,
-                output_tokens_details=OutputTokensDetails(
-                    reasoning_tokens=0,
-                ),
-                total_tokens=25,
-            ),
-        )
+        next(responses),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -2457,7 +2368,10 @@ def failing_tool(message: str) -> str:
     # Find the execute_tool span
     execute_tool_span = None
     for span in spans:
-        if span.get("description", "").startswith("execute_tool failing_tool"):
+        description = span.get("description", "")
+        if description is not None and description.startswith(
+            "execute_tool failing_tool"
+        ):
             execute_tool_span = span
             break
 
@@ -2522,7 +2436,8 @@ async def test_invoke_agent_span_includes_usage_data(
                 ),
                 total_tokens=30,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -2613,7 +2528,8 @@ async def test_ai_client_span_includes_response_model(
                 ),
                 total_tokens=30,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -2700,7 +2616,8 @@ async def test_ai_client_span_response_model_with_chat_completions(
                 ),
                 total_tokens=40,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -2777,7 +2694,8 @@ def calculator(a: int, b: int) -> int:
                 ),
                 total_tokens=15,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     final_response = get_model_response(
@@ -2815,7 +2733,8 @@ def calculator(a: int, b: int) -> int:
                 ),
                 total_tokens=35,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -2903,7 +2822,8 @@ async def test_invoke_agent_span_includes_response_model(
                 ),
                 total_tokens=30,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -2992,7 +2912,8 @@ def calculator(a: int, b: int) -> int:
                 ),
                 total_tokens=15,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     second_response = get_model_response(
@@ -3030,7 +2951,8 @@ def calculator(a: int, b: int) -> int:
                 ),
                 total_tokens=35,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -3162,7 +3084,13 @@ async def test_streaming_span_update_captures_response_data(
 
 
 @pytest.mark.asyncio
-async def test_streaming_ttft_on_chat_span(sentry_init, test_agent, async_iterator):
+async def test_streaming_ttft_on_chat_span(
+    sentry_init,
+    test_agent,
+    get_model_response,
+    async_iterator,
+    server_side_event_chunks,
+):
     """
     Test that time-to-first-token (TTFT) is recorded on chat spans during streaming.
 
@@ -3189,11 +3117,7 @@ async def test_streaming_ttft_on_chat_span(sentry_init, test_agent, async_iterat
         traces_sample_rate=1.0,
     )
 
-    request = httpx.Request(
-        "POST",
-        "/responses",
-    )
-
+    request_headers = {}
     # openai-agents calls with_streaming_response() if available starting with
     # https://github.com/openai/openai-agents-python/commit/159beb56130f7d85192acfd593c9168757984dc0.
     # When using with_streaming_response() the header set below changes the response type:
@@ -3201,12 +3125,10 @@ async def test_streaming_ttft_on_chat_span(sentry_init, test_agent, async_iterat
     if parse_version(OPENAI_AGENTS_VERSION) >= (0, 10, 3) and hasattr(
         agent_with_tool.model._client.responses, "with_streaming_response"
     ):
-        request.headers["X-Stainless-Raw-Response"] = "stream"
+        request_headers["X-Stainless-Raw-Response"] = "stream"
 
-    response = httpx.Response(
-        200,
-        request=request,
-        content=async_iterator(
+    response = get_model_response(
+        async_iterator(
             server_side_event_chunks(
                 [
                     ResponseCreatedEvent(
@@ -3283,6 +3205,7 @@ async def test_streaming_ttft_on_chat_span(sentry_init, test_agent, async_iterat
                 ]
             )
         ),
+        request_headers=request_headers,
     )
 
     # Patching https://github.com/openai/openai-python/blob/656e3cab4a18262a49b961d41293367e45ee71b9/src/openai/_base_client.py#L1604
@@ -3320,7 +3243,11 @@ async def test_streaming_ttft_on_chat_span(sentry_init, test_agent, async_iterat
 )
 @pytest.mark.asyncio
 async def test_conversation_id_on_all_spans(
-    sentry_init, capture_events, test_agent, mock_model_response, get_model_response
+    sentry_init,
+    capture_events,
+    test_agent,
+    nonstreaming_responses_model_response,
+    get_model_response,
 ):
     """
     Test that gen_ai.conversation.id is set on all AI-related spans when passed to Runner.run().
@@ -3330,7 +3257,9 @@ async def test_conversation_id_on_all_spans(
     model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
     agent = test_agent.clone(model=model)
 
-    response = get_model_response(mock_model_response)
+    response = get_model_response(
+        nonstreaming_responses_model_response, serialize_pydantic=True
+    )
 
     with patch.object(
         agent.model._client._client,
@@ -3423,7 +3352,8 @@ def simple_tool(message: str) -> str:
                 ),
                 total_tokens=15,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     final_response = get_model_response(
@@ -3461,7 +3391,8 @@ def simple_tool(message: str) -> str:
                 ),
                 total_tokens=30,
             ),
-        )
+        ),
+        serialize_pydantic=True,
     )
 
     with patch.object(
@@ -3513,7 +3444,7 @@ async def test_no_conversation_id_when_not_provided(
     sentry_init,
     capture_events,
     test_agent,
-    mock_model_response,
+    nonstreaming_responses_model_response,
     get_model_response,
 ):
     """
@@ -3524,7 +3455,9 @@ async def test_no_conversation_id_when_not_provided(
     model = OpenAIResponsesModel(model="gpt-4", openai_client=client)
     agent = test_agent.clone(model=model)
 
-    response = get_model_response(mock_model_response)
+    response = get_model_response(
+        nonstreaming_responses_model_response, serialize_pydantic=True
+    )
 
     with patch.object(
         agent.model._client._client,
diff --git a/tests/integrations/pydantic_ai/test_pydantic_ai.py b/tests/integrations/pydantic_ai/test_pydantic_ai.py
index 52f724a4dc..f0ddc6c4ed 100644
--- a/tests/integrations/pydantic_ai/test_pydantic_ai.py
+++ b/tests/integrations/pydantic_ai/test_pydantic_ai.py
@@ -889,7 +889,7 @@ async def test_mcp_tool_execution_spans(sentry_init, capture_events):
     """
     pytest.importorskip("mcp")
 
-    from unittest.mock import AsyncMock, MagicMock
+    from unittest.mock import MagicMock
     from pydantic_ai.mcp import MCPServerStdio
     from pydantic_ai import Agent
     from pydantic_ai.toolsets.combined import CombinedToolset
@@ -1379,7 +1379,6 @@ async def test_agent_data_from_scope(sentry_init, capture_events):
     """
     Test that agent data can be retrieved from Sentry scope when not passed directly.
     """
-    import sentry_sdk
 
     agent = Agent(
         "test",
@@ -1753,7 +1752,7 @@ async def test_message_parts_with_tool_return(sentry_init, capture_events):
     """
     Test that ToolReturnPart messages are handled correctly.
     """
-    from pydantic_ai import Agent, messages
+    from pydantic_ai import Agent
 
     agent = Agent(
         "test",
@@ -2509,7 +2508,6 @@ async def test_tool_execution_without_span_context(sentry_init, capture_events):
     This tests the code path where current_span is None in _patch_tool_execution.
     """
     # Import the patching function
-    from unittest.mock import AsyncMock, MagicMock
 
     sentry_init(
         integrations=[PydanticAIIntegration()],
diff --git a/tests/integrations/stdlib/test_httplib.py b/tests/integrations/stdlib/test_httplib.py
index ad6b0688b9..cdbf6cd68c 100644
--- a/tests/integrations/stdlib/test_httplib.py
+++ b/tests/integrations/stdlib/test_httplib.py
@@ -1,6 +1,5 @@
 import os
 import datetime
-import socket
 from http.client import HTTPConnection, HTTPSConnection
 from http.server import BaseHTTPRequestHandler, HTTPServer
 from socket import SocketIO
diff --git a/tests/integrations/strawberry/test_strawberry.py b/tests/integrations/strawberry/test_strawberry.py
index ba645da257..d3174ed857 100644
--- a/tests/integrations/strawberry/test_strawberry.py
+++ b/tests/integrations/strawberry/test_strawberry.py
@@ -5,7 +5,6 @@
 pytest.importorskip("fastapi")
 pytest.importorskip("flask")
 
-from unittest import mock
 
 from fastapi import FastAPI
 from fastapi.testclient import TestClient
diff --git a/tests/profiler/test_continuous_profiler.py b/tests/profiler/test_continuous_profiler.py
index e4f5cb5e25..f0c3b5a27f 100644
--- a/tests/profiler/test_continuous_profiler.py
+++ b/tests/profiler/test_continuous_profiler.py
@@ -621,3 +621,67 @@ def test_continuous_profiler_manual_start_and_stop_noop_when_using_trace_lifecyl
     ) as mock_teardown:
         stop_profiler_func()
         mock_teardown.assert_not_called()
+
+
+@mock.patch("sentry_sdk.profiler.continuous_profiler.PROFILE_BUFFER_SECONDS", 0.01)
+def test_continuous_profiler_run_does_not_null_buffer(
+    sentry_init,
+    capture_envelopes,
+    teardown_profiling,
+):
+    """
+    Verifies that ContinuousScheduler.run() does not set self.buffer = None
+    after exiting its sampling loop.
+
+    Previously, run() would execute `self.buffer = None` after the while
+    loop exited. During rapid stop/start cycles, this could race with
+    ensure_running() which creates a new buffer: the old thread's cleanup
+    would destroy the newly-created buffer, causing the new profiler thread
+    to silently drop all samples (self.buffer is None in the sampler).
+
+    The fix uses a local buffer reference for flushing and never sets
+    self.buffer = None from run().
+    """
+    from sentry_sdk.profiler import continuous_profiler as cp
+
+    options = get_client_options(True)(
+        mode="thread", profile_session_sample_rate=1.0, lifecycle="manual"
+    )
+    sentry_init(traces_sample_rate=1.0, **options)
+    envelopes = capture_envelopes()
+    thread = threading.current_thread()
+
+    # Start and verify profiler works
+    start_profiler()
+    envelopes.clear()
+    with sentry_sdk.start_transaction(name="profiling"):
+        with sentry_sdk.start_span(op="op"):
+            time.sleep(0.1)
+    assert_single_transaction_with_profile_chunks(envelopes, thread)
+
+    # Get the scheduler and create a sentinel buffer.
+    # We'll call run() directly to verify it doesn't null out self.buffer.
+    scheduler = cp._scheduler
+    assert scheduler is not None
+
+    # Stop the profiler so the thread exits cleanly
+    stop_profiler()
+
+    # Now set up a fresh buffer and mark the scheduler as not running
+    # (simulating the state right after ensure_running() created a new buffer
+    # but the old thread hasn't done cleanup yet).
+    scheduler.reset_buffer()
+    buffer_before = scheduler.buffer
+    assert buffer_before is not None
+
+    # Simulate what happens when run() exits its while loop:
+    # self.running is already False, so the while loop exits immediately.
+    scheduler.running = False
+    scheduler.run()
+
+    # After the fix, run() should NOT have set self.buffer = None.
+    # It should only flush using a local reference.
+    assert scheduler.buffer is not None, (
+        "run() must not set self.buffer = None; "
+        "this would destroy buffers created by concurrent ensure_running() calls"
+    )
diff --git a/tests/test_ai_integration_deactivation.py b/tests/test_ai_integration_deactivation.py
index b02b64c6ee..683de2f0b2 100644
--- a/tests/test_ai_integration_deactivation.py
+++ b/tests/test_ai_integration_deactivation.py
@@ -190,7 +190,6 @@ def test_langchain_and_openai_both_explicit_both_active(
 def test_no_langchain_means_openai_and_anthropic_can_auto_enable(
     sentry_init, reset_integrations, monkeypatch
 ):
-    import sys
     import sentry_sdk.integrations
 
     old_iter = sentry_sdk.integrations.iter_default_integrations
diff --git a/tests/test_ai_monitoring.py b/tests/test_ai_monitoring.py
index 969d14658d..c9f5c5cdcd 100644
--- a/tests/test_ai_monitoring.py
+++ b/tests/test_ai_monitoring.py
@@ -1,19 +1,14 @@
-import json
-import uuid
-
 import pytest
 
 import sentry_sdk
 from sentry_sdk._types import (
     AnnotatedValue,
-    SENSITIVE_DATA_SUBSTITUTE,
     BLOB_DATA_SUBSTITUTE,
 )
 from sentry_sdk.ai.monitoring import ai_track
 from sentry_sdk.ai.utils import (
     MAX_GEN_AI_MESSAGE_BYTES,
     MAX_SINGLE_MESSAGE_CONTENT_CHARS,
-    set_data_normalized,
     truncate_and_annotate_messages,
     truncate_messages_by_size,
     _find_truncation_index,
@@ -27,7 +22,6 @@
     transform_content_part,
     transform_message_content,
 )
-from sentry_sdk.serializer import serialize
 from sentry_sdk.utils import safe_serialize
 
 
@@ -318,6 +312,105 @@ def test_single_message_truncation(self):
         assert user_msgs[0]["content"].endswith("...")
         assert len(user_msgs[0]["content"]) < len(large_content)
 
+    def test_single_message_truncation_list_content_exceeds_limit(self):
+        """Test that list-based content (e.g. pydantic-ai multimodal format) is truncated."""
+        large_text = "A" * 200_000
+
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": large_text},
+                ],
+            },
+        ]
+
+        result, _ = truncate_messages_by_size(messages)
+
+        text_part = result[0]["content"][0]
+        assert text_part["text"].endswith("...")
+        assert len(text_part["text"]) == MAX_SINGLE_MESSAGE_CONTENT_CHARS + 3
+
+    def test_single_message_truncation_list_content_under_limit(self):
+        """Test that small text parts are preserved when non-text parts push size over byte limit."""
+        short_text = "Hello world"
+        large_data_url = "data:image/png;base64," + "A" * 200_000
+
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": short_text},
+                    {"type": "image_url", "image_url": {"url": large_data_url}},
+                ],
+            },
+        ]
+
+        result, _ = truncate_messages_by_size(messages)
+
+        text_part = result[0]["content"][0]
+        assert text_part["text"] == short_text
+
+    def test_single_message_truncation_list_content_mixed_parts(self):
+        """Test truncation with mixed content types (text + non-text parts)."""
+        max_chars = 50
+        large_data_url = "data:image/png;base64," + "X" * 200_000
+
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": "A" * 30},
+                    {"type": "image_url", "image_url": {"url": large_data_url}},
+                    {"type": "text", "text": "B" * 30},
+                ],
+            },
+        ]
+
+        result, _ = truncate_messages_by_size(
+            messages, max_single_message_chars=max_chars
+        )
+
+        parts = result[0]["content"]
+        # First text part uses 30 chars of the 50 budget
+        assert parts[0]["text"] == "A" * 30
+        # Image part is unchanged
+        assert parts[1]["type"] == "image_url"
+        # Second text part is truncated to remaining 20 chars
+        assert parts[2]["text"] == "B" * 20 + "..."
+
+    def test_single_message_truncation_list_content_multiple_text_parts(self):
+        """Test that budget is distributed across multiple text parts."""
+        max_chars = 10
+        # Two large text parts that together exceed 128KB byte limit
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": "A" * 100_000},
+                    {"type": "text", "text": "B" * 100_000},
+                ],
+            },
+        ]
+
+        result, _ = truncate_messages_by_size(
+            messages, max_single_message_chars=max_chars
+        )
+
+        parts = result[0]["content"]
+        # First part is truncated to the full budget
+        assert parts[0]["text"] == "A" * 10 + "..."
+        # Second part gets truncated to 0 chars + ellipsis
+        assert parts[1]["text"] == "..."
+
+    @pytest.mark.parametrize("content", [None, 42, 3.14, True])
+    def test_single_message_truncation_non_str_non_list_content(self, content):
+        messages = [{"role": "user", "content": content}]
+
+        result, _ = truncate_messages_by_size(messages)
+
+        assert result[0]["content"] is content
+
 
 class TestTruncateAndAnnotateMessages:
     def test_only_keeps_last_message(self, sample_messages):
diff --git a/tests/test_logs.py b/tests/test_logs.py
index d9c8a79f8c..86861cfe90 100644
--- a/tests/test_logs.py
+++ b/tests/test_logs.py
@@ -9,7 +9,7 @@
 import sentry_sdk
 import sentry_sdk.logger
 from sentry_sdk import get_client
-from sentry_sdk.envelope import Envelope, Item, PayloadRef
+from sentry_sdk.envelope import Envelope
 from sentry_sdk.types import Log
 from sentry_sdk.consts import SPANDATA, VERSION
 
@@ -19,8 +19,7 @@
 
 
 def otel_attributes_to_dict(otel_attrs: "Mapping[str, Any]") -> "Mapping[str, Any]":
-    def _convert_attr(attr):
-        # type: (Mapping[str, Union[str, float, bool]]) -> Any
+    def _convert_attr(attr: "Mapping[str, Union[str, float, bool]]") -> "Any":
         if attr["type"] == "boolean":
             return attr["value"]
         if attr["type"] == "double":
@@ -784,3 +783,39 @@ def before_send_log(log, _):
     )
 
     get_client().flush()
+
+
+@minimum_python_37
+@pytest.mark.timeout(5)
+def test_reentrant_add_does_not_deadlock(sentry_init, capture_envelopes):
+    """Adding to the batcher from within a flush must not deadlock.
+
+    This covers the scenario where GC emits a ResourceWarning during
+    _add_to_envelope (or _flush_event.wait/set), and the warning is
+    routed through the logging integration back into batcher.add().
+    See https://github.com/getsentry/sentry-python/issues/5681
+    """
+    sentry_init(enable_logs=True)
+    capture_envelopes()
+
+    client = sentry_sdk.get_client()
+    batcher = client.log_batcher
+
+    reentrant_add_called = False
+    original_add_to_envelope = batcher._add_to_envelope
+
+    def add_to_envelope_with_reentrant_add(envelope):
+        nonlocal reentrant_add_called
+        # Simulate a GC warning routing back into add() during flush
+        batcher.add({"fake": "log"})
+        reentrant_add_called = True
+        original_add_to_envelope(envelope)
+
+    batcher._add_to_envelope = add_to_envelope_with_reentrant_add
+
+    sentry_sdk.logger.warning("test log")
+    client.flush()
+
+    assert reentrant_add_called
+    # If the re-entrancy guard didn't work, this test would hang and it'd
+    # eventually be timed out by pytest-timeout
diff --git a/tests/test_metrics.py b/tests/test_metrics.py
index ada50d645d..3ad3f6042d 100644
--- a/tests/test_metrics.py
+++ b/tests/test_metrics.py
@@ -1,9 +1,6 @@
-import json
-import sys
-from typing import List, Any, Mapping
+from typing import List
 from unittest import mock
 
-import pytest
 
 import sentry_sdk
 from sentry_sdk import get_client
diff --git a/tests/test_shadowed_module.py b/tests/test_shadowed_module.py
index 10d86f285b..8beb93dc36 100644
--- a/tests/test_shadowed_module.py
+++ b/tests/test_shadowed_module.py
@@ -7,7 +7,6 @@
 import pytest
 
 from sentry_sdk import integrations
-from sentry_sdk.integrations import _DEFAULT_INTEGRATIONS, Integration
 
 
 def pytest_generate_tests(metafunc):
diff --git a/tests/test_spotlight.py b/tests/test_spotlight.py
index f554ff7c5b..1e304e5e54 100644
--- a/tests/test_spotlight.py
+++ b/tests/test_spotlight.py
@@ -1,7 +1,6 @@
 import pytest
 
 import sentry_sdk
-from sentry_sdk.spotlight import DEFAULT_SPOTLIGHT_URL
 
 
 @pytest.fixture
diff --git a/tests/test_utils.py b/tests/test_utils.py
index 1fc651f805..0fa116a57e 100644
--- a/tests/test_utils.py
+++ b/tests/test_utils.py
@@ -7,7 +7,6 @@
 import pytest
 
 import sentry_sdk
-from sentry_sdk._compat import PY38
 from sentry_sdk.integrations import Integration
 from sentry_sdk._queue import Queue
 from sentry_sdk.utils import (
@@ -942,14 +941,12 @@ def target():
     assert (main_thread.ident, main_thread.name) == results.get(timeout=1)
 
 
-@pytest.mark.skipif(PY38, reason="Flakes a lot on 3.8 in CI.")
 def test_get_current_thread_meta_failed_to_get_main_thread():
     results = Queue(maxsize=1)
 
     def target():
-        with mock.patch("threading.current_thread", side_effect=["fake thread"]):
-            with mock.patch("threading.current_thread", side_effect=["fake thread"]):
-                results.put(get_current_thread_meta())
+        with mock.patch("threading.current_thread", return_value="fake thread"):
+            results.put(get_current_thread_meta())
 
     main_thread = threading.main_thread()
 
diff --git a/tests/tracing/test_decorator.py b/tests/tracing/test_decorator.py
index 70dc186ba0..15432f5862 100644
--- a/tests/tracing/test_decorator.py
+++ b/tests/tracing/test_decorator.py
@@ -1,5 +1,4 @@
 import inspect
-import sys
 from unittest import mock
 
 import pytest
diff --git a/tests/tracing/test_deprecated.py b/tests/tracing/test_deprecated.py
index ac3b8d7463..f030a465ff 100644
--- a/tests/tracing/test_deprecated.py
+++ b/tests/tracing/test_deprecated.py
@@ -4,9 +4,6 @@
 
 import sentry_sdk
 import sentry_sdk.tracing
-from sentry_sdk import start_span
-
-from sentry_sdk.tracing import Span
 
 
 @pytest.mark.parametrize(
diff --git a/tests/tracing/test_sampling.py b/tests/tracing/test_sampling.py
index c0f307ecf7..93c1106c99 100644
--- a/tests/tracing/test_sampling.py
+++ b/tests/tracing/test_sampling.py
@@ -5,7 +5,7 @@
 import pytest
 
 import sentry_sdk
-from sentry_sdk import start_span, start_transaction, capture_exception, continue_trace
+from sentry_sdk import start_span, start_transaction, capture_exception
 from sentry_sdk.tracing_utils import Baggage
 from sentry_sdk.utils import logger
 
diff --git a/tests/tracing/test_span_streaming.py b/tests/tracing/test_span_streaming.py
index eb9446c1ee..21c3d26ea3 100644
--- a/tests/tracing/test_span_streaming.py
+++ b/tests/tracing/test_span_streaming.py
@@ -1,12 +1,14 @@
 import asyncio
 import re
 import sys
+import time
 from typing import Any
 from unittest import mock
 
 import pytest
 
 import sentry_sdk
+from sentry_sdk.profiler.continuous_profiler import get_profiler_id
 from sentry_sdk.traces import NoOpStreamedSpan, SpanStatus, StreamedSpan
 
 minimum_python_38 = pytest.mark.skipif(
@@ -639,6 +641,59 @@ def test_continue_trace_unsampled(sentry_init, capture_envelopes):
     assert len(spans) == 0
 
 
+def test_unsampled_spans_produce_client_report(
+    sentry_init, capture_envelopes, capture_record_lost_event_calls
+):
+    sentry_init(
+        traces_sample_rate=0.0,
+        _experiments={"trace_lifecycle": "stream"},
+    )
+
+    envelopes = capture_envelopes()
+    record_lost_event_calls = capture_record_lost_event_calls()
+
+    with sentry_sdk.traces.start_span(name="segment"):
+        with sentry_sdk.traces.start_span(name="child1"):
+            pass
+        with sentry_sdk.traces.start_span(name="child2"):
+            pass
+
+    sentry_sdk.get_client().flush()
+
+    spans = envelopes_to_spans(envelopes)
+    assert not spans
+
+    assert record_lost_event_calls == [
+        ("sample_rate", "span", None, 1),
+        ("sample_rate", "span", None, 1),
+        ("sample_rate", "span", None, 1),
+    ]
+
+
+def test_no_client_reports_if_tracing_is_off(
+    sentry_init, capture_envelopes, capture_record_lost_event_calls
+):
+    sentry_init(
+        traces_sample_rate=None,
+        _experiments={"trace_lifecycle": "stream"},
+    )
+
+    envelopes = capture_envelopes()
+    record_lost_event_calls = capture_record_lost_event_calls()
+
+    with sentry_sdk.traces.start_span(name="segment"):
+        with sentry_sdk.traces.start_span(name="child1"):
+            pass
+        with sentry_sdk.traces.start_span(name="child2"):
+            pass
+
+    sentry_sdk.get_client().flush()
+
+    spans = envelopes_to_spans(envelopes)
+    assert not spans
+    assert not record_lost_event_calls
+
+
 def test_continue_trace_no_sample_rand(sentry_init, capture_envelopes):
     sentry_init(
         # parent sampling decision takes precedence over traces_sample_rate
@@ -678,6 +733,67 @@ def test_continue_trace_no_sample_rand(sentry_init, capture_envelopes):
     assert segment["trace_id"] == trace_id
 
 
+def test_outgoing_traceparent_and_baggage(sentry_init, capture_envelopes):
+    sentry_init(
+        traces_sample_rate=1.0,
+        _experiments={"trace_lifecycle": "stream"},
+    )
+
+    sentry_sdk.traces.new_trace()
+
+    with sentry_sdk.traces.start_span(name="span") as span:
+        assert span.sampled is True
+
+        trace_id = span.trace_id
+        span_id = span.span_id
+
+        traceparent = sentry_sdk.get_traceparent()
+        assert traceparent == f"{trace_id}-{span_id}-1"
+
+        baggage = sentry_sdk.get_baggage()
+        baggage_items = dict(tuple(item.split("=")) for item in baggage.split(","))
+        assert "sentry-trace_id" in baggage_items
+        assert baggage_items["sentry-trace_id"] == trace_id
+        assert "sentry-sampled" in baggage_items
+        assert baggage_items["sentry-sampled"] == "true"
+
+
+def test_outgoing_traceparent_and_baggage_when_noop_span_is_active(
+    sentry_init, capture_envelopes
+):
+    sentry_init(
+        traces_sample_rate=1.0,
+        _experiments={
+            "trace_lifecycle": "stream",
+            "ignore_spans": ["ignored"],
+        },
+    )
+
+    sentry_sdk.traces.new_trace()
+
+    propagation_context = (
+        sentry_sdk.get_current_scope().get_active_propagation_context()
+    )
+    propagation_trace_id = propagation_context.trace_id
+    propagation_span_id = propagation_context.span_id
+
+    with sentry_sdk.traces.start_span(name="ignored") as span:
+        assert span.sampled is False
+
+        noop_trace_id = span.trace_id
+        noop_span_id = span.span_id
+
+        traceparent = sentry_sdk.get_traceparent()
+        assert traceparent != f"{noop_trace_id}-{noop_span_id}"
+        assert traceparent == f"{propagation_trace_id}-{propagation_span_id}"
+
+        baggage = sentry_sdk.get_baggage()
+        baggage_items = dict(tuple(item.split("=")) for item in baggage.split(","))
+        assert "sentry-trace_id" in baggage_items
+        assert baggage_items["sentry-trace_id"] != noop_trace_id
+        assert baggage_items["sentry-trace_id"] == propagation_trace_id
+
+
 def test_trace_decorator(sentry_init, capture_envelopes):
     sentry_init(
         traces_sample_rate=1.0,
@@ -880,6 +996,23 @@ def test_set_span_status_on_error(sentry_init, capture_envelopes):
     assert span["status"] == "error"
 
 
+def test_set_span_status_on_ignored_span(sentry_init, capture_envelopes):
+    sentry_init(
+        traces_sample_rate=1.0,
+        _experiments={"trace_lifecycle": "stream", "ignore_spans": ["ignored"]},
+    )
+
+    events = capture_envelopes()
+
+    with sentry_sdk.traces.start_span(name="ignored") as span:
+        span.status = "error"
+
+    sentry_sdk.get_client().flush()
+    spans = envelopes_to_spans(events)
+
+    assert len(spans) == 0
+
+
 @pytest.mark.parametrize(
     ("ignore_spans", "name", "attributes", "ignored"),
     [
@@ -1244,6 +1377,132 @@ def test_ignore_spans_reparenting(sentry_init, capture_envelopes):
     assert span5["parent_span_id"] == span3["span_id"]
 
 
+def test_ignored_spans_produce_client_report(
+    sentry_init, capture_envelopes, capture_record_lost_event_calls
+):
+    sentry_init(
+        traces_sample_rate=1.0,
+        _experiments={"trace_lifecycle": "stream", "ignore_spans": ["ignored"]},
+    )
+
+    envelopes = capture_envelopes()
+    record_lost_event_calls = capture_record_lost_event_calls()
+
+    with sentry_sdk.traces.start_span(name="ignored"):
+        with sentry_sdk.traces.start_span(name="span1"):
+            pass
+        with sentry_sdk.traces.start_span(name="span2"):
+            pass
+
+    sentry_sdk.get_client().flush()
+
+    spans = envelopes_to_spans(envelopes)
+    assert not spans
+
+    # All three spans will be ignored since the segment is ignored
+    assert record_lost_event_calls == [
+        ("ignored", "span", None, 1),
+        ("ignored", "span", None, 1),
+        ("ignored", "span", None, 1),
+    ]
+
+
+@mock.patch("sentry_sdk.profiler.continuous_profiler.DEFAULT_SAMPLING_FREQUENCY", 21)
+def test_segment_span_has_profiler_id(
+    sentry_init, capture_envelopes, teardown_profiling
+):
+    sentry_init(
+        traces_sample_rate=1.0,
+        profile_lifecycle="trace",
+        profiler_mode="thread",
+        profile_session_sample_rate=1.0,
+        _experiments={
+            "trace_lifecycle": "stream",
+            "continuous_profiling_auto_start": True,
+        },
+    )
+    envelopes = capture_envelopes()
+
+    with sentry_sdk.traces.start_span(name="profiled segment"):
+        time.sleep(0.1)
+
+    sentry_sdk.get_client().flush()
+    time.sleep(0.3)  # wait for profiler to flush
+
+    spans = envelopes_to_spans(envelopes)
+    assert len(spans) == 1
+    assert "sentry.profiler_id" in spans[0]["attributes"]
+
+    profile_chunks = [
+        item
+        for envelope in envelopes
+        for item in envelope.items
+        if item.type == "profile_chunk"
+    ]
+    assert len(profile_chunks) > 0
+
+
+def test_segment_span_no_profiler_id_when_unsampled(
+    sentry_init, capture_envelopes, teardown_profiling
+):
+    sentry_init(
+        traces_sample_rate=1.0,
+        profile_lifecycle="trace",
+        profiler_mode="thread",
+        profile_session_sample_rate=0.0,
+        _experiments={
+            "trace_lifecycle": "stream",
+            "continuous_profiling_auto_start": True,
+        },
+    )
+    envelopes = capture_envelopes()
+
+    with sentry_sdk.traces.start_span(name="segment"):
+        time.sleep(0.05)
+
+    sentry_sdk.get_client().flush()
+    time.sleep(0.2)
+
+    spans = envelopes_to_spans(envelopes)
+    assert len(spans) == 1
+    assert "sentry.profiler_id" not in spans[0]["attributes"]
+
+    profile_chunks = [
+        item
+        for envelope in envelopes
+        for item in envelope.items
+        if item.type == "profile_chunk"
+    ]
+    assert len(profile_chunks) == 0
+
+
+@mock.patch("sentry_sdk.profiler.continuous_profiler.DEFAULT_SAMPLING_FREQUENCY", 21)
+def test_profile_stops_when_segment_ends(
+    sentry_init, capture_envelopes, teardown_profiling
+):
+    sentry_init(
+        traces_sample_rate=1.0,
+        profile_lifecycle="trace",
+        profiler_mode="thread",
+        profile_session_sample_rate=1.0,
+        _experiments={
+            "trace_lifecycle": "stream",
+            "continuous_profiling_auto_start": True,
+        },
+    )
+    capture_envelopes()
+
+    with sentry_sdk.traces.start_span(name="segment") as span:
+        time.sleep(0.1)
+        assert span._continuous_profile is not None
+        assert span._continuous_profile.active is True
+
+    assert span._continuous_profile.active is False
+
+    time.sleep(0.3)
+    assert get_profiler_id() is None, "profiler should have stopped"
+
+
 def test_transport_format(sentry_init, capture_envelopes):
     sentry_init(
         server_name="test-server",
diff --git a/tox.ini b/tox.ini
index 3f8ae2b530..030dfcba3f 100644
--- a/tox.ini
+++ b/tox.ini
@@ -60,81 +60,91 @@ envlist =
     {py3.10,py3.12,py3.13}-mcp-v1.19.0
     {py3.10,py3.12,py3.13}-mcp-v1.23.3
     {py3.10,py3.12,py3.13}-mcp-v1.26.0
+    {py3.10,py3.12,py3.13}-mcp-latest
 
     {py3.10,py3.13,py3.14,py3.14t}-fastmcp-v0.1.0
     {py3.10,py3.13,py3.14,py3.14t}-fastmcp-v0.4.1
     {py3.10,py3.13,py3.14,py3.14t}-fastmcp-v1.0
     {py3.10,py3.12,py3.13}-fastmcp-v2.14.5
-    {py3.10,py3.12,py3.13}-fastmcp-v3.1.0
+    {py3.10,py3.12,py3.13}-fastmcp-v3.1.1
+    {py3.10,py3.12,py3.13}-fastmcp-latest
 
 
     # ~~~ Agents ~~~
     {py3.10,py3.11,py3.12}-openai_agents-v0.0.19
     {py3.10,py3.12,py3.13}-openai_agents-v0.4.2
     {py3.10,py3.13,py3.14,py3.14t}-openai_agents-v0.8.4
-    {py3.10,py3.13,py3.14,py3.14t}-openai_agents-v0.11.1
+    {py3.10,py3.13,py3.14,py3.14t}-openai_agents-v0.13.0
+    {py3.10,py3.13,py3.14,py3.14t}-openai_agents-latest
 
     {py3.10,py3.12,py3.13}-pydantic_ai-v1.0.18
-    {py3.10,py3.12,py3.13}-pydantic_ai-v1.22.0
-    {py3.10,py3.12,py3.13}-pydantic_ai-v1.44.0
-    {py3.10,py3.13,py3.14}-pydantic_ai-v1.67.0
+    {py3.10,py3.12,py3.13}-pydantic_ai-v1.23.0
+    {py3.10,py3.12,py3.13}-pydantic_ai-v1.47.0
+    {py3.10,py3.13,py3.14}-pydantic_ai-v1.70.0
+    {py3.10,py3.13,py3.14}-pydantic_ai-latest
 
 
     # ~~~ AI Workflow ~~~
     {py3.9,py3.11,py3.12}-langchain-base-v0.1.20
     {py3.9,py3.12,py3.13}-langchain-base-v0.3.28
-    {py3.10,py3.13,py3.14}-langchain-base-v1.2.10
+    {py3.10,py3.13,py3.14}-langchain-base-v1.2.13
+    {py3.10,py3.13,py3.14}-langchain-base-latest
 
     {py3.9,py3.11,py3.12}-langchain-notiktoken-v0.1.20
     {py3.9,py3.12,py3.13}-langchain-notiktoken-v0.3.28
-    {py3.10,py3.13,py3.14}-langchain-notiktoken-v1.2.10
+    {py3.10,py3.13,py3.14}-langchain-notiktoken-v1.2.13
+    {py3.10,py3.13,py3.14}-langchain-notiktoken-latest
 
     {py3.9,py3.13,py3.14}-langgraph-v0.6.11
-    {py3.10,py3.12,py3.13}-langgraph-v1.0.10
+    {py3.10,py3.12,py3.13}-langgraph-v1.1.3
+    {py3.10,py3.12,py3.13}-langgraph-latest
 
 
     # ~~~ AI ~~~
     {py3.8,py3.11,py3.12}-anthropic-v0.16.0
     {py3.8,py3.11,py3.12}-anthropic-v0.39.0
     {py3.8,py3.12,py3.13}-anthropic-v0.62.0
-    {py3.9,py3.13,py3.14,py3.14t}-anthropic-v0.84.0
+    {py3.9,py3.13,py3.14,py3.14t}-anthropic-v0.86.0
+    {py3.9,py3.13,py3.14,py3.14t}-anthropic-latest
 
     {py3.9,py3.10,py3.11}-cohere-v5.4.0
     {py3.9,py3.11,py3.12}-cohere-v5.10.0
     {py3.9,py3.11,py3.12}-cohere-v5.15.0
     {py3.9,py3.13,py3.14}-cohere-v5.20.7
+    {py3.9,py3.13,py3.14}-cohere-latest
 
     {py3.9,py3.12,py3.13}-google_genai-v1.29.0
-    {py3.9,py3.12,py3.13}-google_genai-v1.41.0
-    {py3.10,py3.13,py3.14,py3.14t}-google_genai-v1.53.0
-    {py3.10,py3.13,py3.14,py3.14t}-google_genai-v1.66.0
+    {py3.9,py3.12,py3.13}-google_genai-v1.42.0
+    {py3.10,py3.13,py3.14,py3.14t}-google_genai-v1.55.0
+    {py3.10,py3.13,py3.14,py3.14t}-google_genai-v1.68.0
+    {py3.10,py3.13,py3.14,py3.14t}-google_genai-latest
 
     {py3.8,py3.10,py3.11}-huggingface_hub-v0.24.7
     {py3.8,py3.12,py3.13}-huggingface_hub-v0.36.2
-    {py3.9,py3.13,py3.14,py3.14t}-huggingface_hub-v1.6.0
-
-    {py3.9,py3.12,py3.13}-litellm-v1.77.7
-    {py3.9,py3.12,py3.13}-litellm-v1.79.3
-    {py3.9,py3.12,py3.13}-litellm-v1.81.16
-    {py3.9,py3.12,py3.13}-litellm-v1.82.0
+    {py3.9,py3.13,py3.14,py3.14t}-huggingface_hub-v1.7.2
+    {py3.9,py3.13,py3.14,py3.14t}-huggingface_hub-latest
 
     {py3.8,py3.11,py3.12}-openai-base-v1.0.1
     {py3.8,py3.12,py3.13}-openai-base-v1.109.1
-    {py3.9,py3.13,py3.14,py3.14t}-openai-base-v2.26.0
+    {py3.9,py3.13,py3.14,py3.14t}-openai-base-v2.29.0
+    {py3.9,py3.13,py3.14,py3.14t}-openai-base-latest
 
     {py3.8,py3.11,py3.12}-openai-notiktoken-v1.0.1
     {py3.8,py3.12,py3.13}-openai-notiktoken-v1.109.1
-    {py3.9,py3.13,py3.14,py3.14t}-openai-notiktoken-v2.26.0
+    {py3.9,py3.13,py3.14,py3.14t}-openai-notiktoken-v2.29.0
+    {py3.9,py3.13,py3.14,py3.14t}-openai-notiktoken-latest
 
 
     # ~~~ Cloud ~~~
     {py3.6,py3.7}-boto3-v1.12.49
     {py3.6,py3.9,py3.10}-boto3-v1.21.46
     {py3.7,py3.11,py3.12}-boto3-v1.33.13
-    {py3.9,py3.13,py3.14,py3.14t}-boto3-v1.42.63
+    {py3.9,py3.13,py3.14,py3.14t}-boto3-v1.42.74
+    {py3.9,py3.13,py3.14,py3.14t}-boto3-latest
 
     {py3.6,py3.7,py3.8}-chalice-v1.16.0
     {py3.9,py3.12,py3.13}-chalice-v1.32.0
+    {py3.9,py3.12,py3.13}-chalice-latest
 
 
     # ~~~ DBs ~~~
@@ -142,56 +152,71 @@ envlist =
     {py3.7,py3.9,py3.10}-asyncpg-v0.26.0
     {py3.8,py3.11,py3.12}-asyncpg-v0.29.0
     {py3.9,py3.13,py3.14,py3.14t}-asyncpg-v0.31.0
+    {py3.9,py3.13,py3.14,py3.14t}-asyncpg-latest
 
     {py3.9,py3.13,py3.14}-clickhouse_driver-v0.2.10
+    {py3.9,py3.13,py3.14}-clickhouse_driver-latest
 
     {py3.6}-pymongo-v3.5.1
     {py3.6,py3.10,py3.11}-pymongo-v3.13.0
     {py3.9,py3.13,py3.14,py3.14t}-pymongo-v4.16.0
+    {py3.9,py3.13,py3.14,py3.14t}-pymongo-latest
 
     {py3.6}-redis-v2.10.6
     {py3.6,py3.7,py3.8}-redis-v3.5.3
     {py3.7,py3.10,py3.11}-redis-v4.6.0
     {py3.8,py3.11,py3.12}-redis-v5.3.1
     {py3.9,py3.12,py3.13}-redis-v6.4.0
-    {py3.10,py3.13,py3.14,py3.14t}-redis-v7.3.0
+    {py3.10,py3.13,py3.14,py3.14t}-redis-v7.4.0
+    {py3.10,py3.13,py3.14,py3.14t}-redis-latest
 
     {py3.6}-redis_py_cluster_legacy-v1.3.6
     {py3.6,py3.7,py3.8}-redis_py_cluster_legacy-v2.1.3
+    {py3.6,py3.7,py3.8}-redis_py_cluster_legacy-latest
 
     {py3.6,py3.8,py3.9}-sqlalchemy-v1.2.19
     {py3.6,py3.11,py3.12}-sqlalchemy-v1.4.54
     {py3.7,py3.12,py3.13}-sqlalchemy-v2.0.48
     {py3.10,py3.13,py3.14,py3.14t}-sqlalchemy-v2.1.0b1
+    {py3.7,py3.12,py3.13}-sqlalchemy-latest
 
 
     # ~~~ Flags ~~~
     {py3.8,py3.12,py3.13}-launchdarkly-v9.8.1
     {py3.10,py3.13,py3.14,py3.14t}-launchdarkly-v9.15.0
+    {py3.10,py3.13,py3.14,py3.14t}-launchdarkly-latest
 
     {py3.8,py3.13,py3.14,py3.14t}-openfeature-v0.7.5
     {py3.9,py3.13,py3.14,py3.14t}-openfeature-v0.8.4
+    {py3.9,py3.13,py3.14,py3.14t}-openfeature-latest
 
     {py3.7,py3.13,py3.14}-statsig-v0.55.3
-    {py3.7,py3.13,py3.14}-statsig-v0.70.5
+    {py3.7,py3.13,py3.14}-statsig-v0.71.6
+    {py3.7,py3.13,py3.14}-statsig-latest
 
     {py3.8,py3.12,py3.13}-unleash-v6.0.1
-    {py3.8,py3.12,py3.13}-unleash-v6.6.0
+    {py3.8,py3.12,py3.13}-unleash-v6.7.0
+    {py3.8,py3.12,py3.13}-unleash-latest
 
 
     # ~~~ GraphQL ~~~
     {py3.8,py3.10,py3.11}-ariadne-v0.20.1
-    {py3.10,py3.13,py3.14,py3.14t}-ariadne-v0.29.0
+    {py3.10,py3.13,py3.14,py3.14t}-ariadne-v1.0.0
+    {py3.10,py3.13,py3.14,py3.14t}-ariadne-v1.1.0a1
+    {py3.10,py3.13,py3.14,py3.14t}-ariadne-latest
 
     {py3.6,py3.9,py3.10}-gql-v3.4.1
     {py3.9,py3.12,py3.13}-gql-v4.0.0
     {py3.9,py3.13,py3.14,py3.14t}-gql-v4.3.0b0
+    {py3.9,py3.12,py3.13}-gql-latest
 
     {py3.6,py3.9,py3.10}-graphene-v3.3
     {py3.8,py3.12,py3.13}-graphene-v3.4.3
+    {py3.8,py3.12,py3.13}-graphene-latest
 
     {py3.8,py3.10,py3.11}-strawberry-v0.209.8
-    {py3.10,py3.13,py3.14,py3.14t}-strawberry-v0.311.0
+    {py3.10,py3.13,py3.14,py3.14t}-strawberry-v0.312.0
+    {py3.10,py3.13,py3.14,py3.14t}-strawberry-latest
 
 
     # ~~~ Network ~~~
@@ -199,43 +224,56 @@ envlist =
     {py3.7,py3.9,py3.10}-grpc-v1.47.5
     {py3.7,py3.11,py3.12}-grpc-v1.62.3
     {py3.9,py3.13,py3.14}-grpc-v1.78.0
+    {py3.9,py3.13,py3.14}-grpc-v1.80.0rc1
+    {py3.9,py3.13,py3.14}-grpc-latest
 
     {py3.6,py3.8,py3.9}-httpx-v0.16.1
     {py3.6,py3.9,py3.10}-httpx-v0.20.0
     {py3.7,py3.10,py3.11}-httpx-v0.24.1
     {py3.9,py3.11,py3.12}-httpx-v0.28.1
+    {py3.9,py3.11,py3.12}-httpx-latest
 
     {py3.6}-requests-v2.12.5
     {py3.9,py3.13,py3.14,py3.14t}-requests-v2.32.5
+    {py3.9,py3.13,py3.14,py3.14t}-requests-latest
 
 
     # ~~~ Tasks ~~~
     {py3.7,py3.9,py3.10}-arq-v0.23
     {py3.9,py3.12,py3.13}-arq-v0.27.0
+    {py3.9,py3.12,py3.13}-arq-latest
 
     {py3.7}-beam-v2.14.0
     {py3.10,py3.12,py3.13}-beam-v2.71.0
+    {py3.10,py3.12,py3.13}-beam-v2.72.0rc2
+    {py3.10,py3.12,py3.13}-beam-latest
 
     {py3.6,py3.7,py3.8}-celery-v4.4.7
     {py3.9,py3.12,py3.13}-celery-v5.6.2
+    {py3.9,py3.12,py3.13}-celery-latest
 
     {py3.6,py3.7}-dramatiq-v1.9.0
     {py3.10,py3.13,py3.14,py3.14t}-dramatiq-v2.1.0
+    {py3.10,py3.13,py3.14,py3.14t}-dramatiq-latest
 
     {py3.6,py3.7}-huey-v2.1.3
     {py3.6,py3.13,py3.14,py3.14t}-huey-v2.6.0
+    {py3.6,py3.13,py3.14,py3.14t}-huey-latest
 
     {py3.9,py3.10}-ray-v2.7.2
     {py3.10,py3.12,py3.13}-ray-v2.54.0
+    {py3.10,py3.12,py3.13}-ray-latest
 
     {py3.6}-rq-v0.6.0
     {py3.6,py3.7}-rq-v0.13.0
     {py3.7,py3.11,py3.12}-rq-v1.16.2
     {py3.9,py3.13,py3.14,py3.14t}-rq-v2.7.0
+    {py3.9,py3.13,py3.14,py3.14t}-rq-latest
 
     {py3.8,py3.9}-spark-v3.0.3
     {py3.8,py3.10,py3.11}-spark-v3.5.8
     {py3.10,py3.13,py3.14}-spark-v4.1.1
+    {py3.10,py3.13,py3.14}-spark-latest
 
 
     # ~~~ Web 1 ~~~
@@ -245,21 +283,23 @@ envlist =
     {py3.8,py3.11,py3.12}-django-v4.2.29
     {py3.10,py3.13,py3.14,py3.14t}-django-v5.2.12
     {py3.12,py3.13,py3.14,py3.14t}-django-v6.0.3
+    {py3.12,py3.13,py3.14,py3.14t}-django-latest
 
     {py3.6,py3.7,py3.8}-flask-v1.1.4
     {py3.8,py3.13,py3.14,py3.14t}-flask-v2.3.3
     {py3.9,py3.13,py3.14,py3.14t}-flask-v3.1.3
+    {py3.9,py3.13,py3.14,py3.14t}-flask-latest
 
     {py3.6,py3.9,py3.10}-starlette-v0.16.0
-    {py3.7,py3.10,py3.11}-starlette-v0.28.0
-    {py3.8,py3.12,py3.13}-starlette-v0.40.0
     {py3.10,py3.13,py3.14,py3.14t}-starlette-v0.52.1
-    {py3.10,py3.13,py3.14,py3.14t}-starlette-v1.0.0rc1
+    {py3.10,py3.13,py3.14,py3.14t}-starlette-v1.0.0
+    {py3.10,py3.13,py3.14,py3.14t}-starlette-latest
 
     {py3.6,py3.9,py3.10}-fastapi-v0.79.1
     {py3.7,py3.10,py3.11}-fastapi-v0.98.0
     {py3.8,py3.12,py3.13}-fastapi-v0.117.1
-    {py3.10,py3.13,py3.14,py3.14t}-fastapi-v0.135.1
+    {py3.10,py3.13,py3.14,py3.14t}-fastapi-v0.135.2
+    {py3.10,py3.13,py3.14,py3.14t}-fastapi-latest
 
 
     # ~~~ Web 2 ~~~
@@ -267,54 +307,66 @@ envlist =
     {py3.7,py3.8,py3.9}-aiohttp-v3.7.4
     {py3.8,py3.12,py3.13}-aiohttp-v3.10.11
     {py3.9,py3.13,py3.14,py3.14t}-aiohttp-v3.13.3
+    {py3.9,py3.13,py3.14,py3.14t}-aiohttp-latest
 
     {py3.6,py3.7}-bottle-v0.12.25
     {py3.8,py3.12,py3.13}-bottle-v0.13.4
+    {py3.8,py3.12,py3.13}-bottle-latest
 
     {py3.6}-falcon-v1.4.1
     {py3.6,py3.7}-falcon-v2.0.0
     {py3.6,py3.11,py3.12}-falcon-v3.1.3
     {py3.9,py3.11,py3.12}-falcon-v4.2.0
+    {py3.9,py3.11,py3.12}-falcon-latest
 
     {py3.8,py3.10,py3.11}-litestar-v2.0.1
     {py3.8,py3.11,py3.12}-litestar-v2.7.2
     {py3.8,py3.12,py3.13}-litestar-v2.14.0
     {py3.8,py3.12,py3.13}-litestar-v2.21.1
+    {py3.8,py3.12,py3.13}-litestar-latest
 
     {py3.6}-pyramid-v1.8.6
     {py3.6,py3.8,py3.9}-pyramid-v1.10.8
-    {py3.6,py3.10,py3.11}-pyramid-v2.0.2
-    {py3.10,py3.13,py3.14}-pyramid-v2.1a1
+    {py3.10,py3.13,py3.14}-pyramid-v2.1
+    {py3.10,py3.13,py3.14}-pyramid-latest
 
     {py3.7,py3.9,py3.10}-quart-v0.16.3
     {py3.9,py3.13,py3.14,py3.14t}-quart-v0.20.0
+    {py3.9,py3.13,py3.14,py3.14t}-quart-latest
 
     {py3.6}-sanic-v0.8.3
     {py3.6,py3.8,py3.9}-sanic-v20.12.7
     {py3.8,py3.10,py3.11}-sanic-v23.12.2
     {py3.10,py3.13,py3.14}-sanic-v25.12.0
+    {py3.10,py3.13,py3.14}-sanic-latest
 
     {py3.8,py3.10,py3.11}-starlite-v1.48.1
     {py3.8,py3.10,py3.11}-starlite-v1.51.16
+    {py3.8,py3.10,py3.11}-starlite-latest
 
     {py3.6,py3.7,py3.8}-tornado-v6.0.4
-    {py3.9,py3.12,py3.13}-tornado-v6.5.4
+    {py3.9,py3.12,py3.13}-tornado-v6.5.5
+    {py3.9,py3.12,py3.13}-tornado-latest
 
 
     # ~~~ Misc ~~~
     {py3.6,py3.12,py3.13}-loguru-v0.7.3
+    {py3.6,py3.12,py3.13}-loguru-latest
 
     {py3.6,py3.7,py3.8}-pure_eval-v0.0.3
     {py3.7,py3.12,py3.13}-pure_eval-v0.2.3
+    {py3.7,py3.12,py3.13}-pure_eval-latest
 
     {py3.6}-trytond-v4.6.22
     {py3.6}-trytond-v4.8.18
     {py3.6,py3.7,py3.8}-trytond-v5.8.16
     {py3.8,py3.10,py3.11}-trytond-v6.8.17
-    {py3.9,py3.12,py3.13}-trytond-v7.8.5
+    {py3.9,py3.12,py3.13}-trytond-v7.8.6
+    {py3.9,py3.12,py3.13}-trytond-latest
 
     {py3.7,py3.12,py3.13}-typer-v0.15.4
     {py3.10,py3.13,py3.14,py3.14t}-typer-v0.24.1
+    {py3.10,py3.13,py3.14,py3.14t}-typer-latest
 
 
 
@@ -390,13 +442,15 @@ deps =
     mcp-v1.19.0: mcp==1.19.0
     mcp-v1.23.3: mcp==1.23.3
     mcp-v1.26.0: mcp==1.26.0
+    mcp-latest: mcp==1.26.0
     mcp: pytest-asyncio
 
     fastmcp-v0.1.0: fastmcp==0.1.0
     fastmcp-v0.4.1: fastmcp==0.4.1
     fastmcp-v1.0: fastmcp==1.0
     fastmcp-v2.14.5: fastmcp==2.14.5
-    fastmcp-v3.1.0: fastmcp==3.1.0
+    fastmcp-v3.1.1: fastmcp==3.1.1
+    fastmcp-latest: fastmcp==3.1.1
     fastmcp: pytest-asyncio
 
 
@@ -404,47 +458,57 @@ deps =
     openai_agents-v0.0.19: openai-agents==0.0.19
     openai_agents-v0.4.2: openai-agents==0.4.2
     openai_agents-v0.8.4: openai-agents==0.8.4
-    openai_agents-v0.11.1: openai-agents==0.11.1
+    openai_agents-v0.13.0: openai-agents==0.13.0
+    openai_agents-latest: openai-agents==0.13.0
     openai_agents: pytest-asyncio
 
     pydantic_ai-v1.0.18: pydantic-ai==1.0.18
-    pydantic_ai-v1.22.0: pydantic-ai==1.22.0
-    pydantic_ai-v1.44.0: pydantic-ai==1.44.0
-    pydantic_ai-v1.67.0: pydantic-ai==1.67.0
+    pydantic_ai-v1.23.0: pydantic-ai==1.23.0
+    pydantic_ai-v1.47.0: pydantic-ai==1.47.0
+    pydantic_ai-v1.70.0: pydantic-ai==1.70.0
+    pydantic_ai-latest: pydantic-ai==1.70.0
     pydantic_ai: pytest-asyncio
 
 
     # ~~~ AI Workflow ~~~
     langchain-base-v0.1.20: langchain==0.1.20
     langchain-base-v0.3.28: langchain==0.3.28
-    langchain-base-v1.2.10: langchain==1.2.10
+    langchain-base-v1.2.13: langchain==1.2.13
+    langchain-base-latest: langchain==1.2.13
     langchain-base: pytest-asyncio
     langchain-base: openai
     langchain-base: tiktoken
     langchain-base: langchain-openai
     langchain-base-v0.3.28: langchain-community
-    langchain-base-v1.2.10: langchain-community
-    langchain-base-v1.2.10: langchain-classic
+    langchain-base-v1.2.13: langchain-community
+    langchain-base-v1.2.13: langchain-classic
+    langchain-base-latest: langchain-community
+    langchain-base-latest: langchain-classic
 
     langchain-notiktoken-v0.1.20: langchain==0.1.20
     langchain-notiktoken-v0.3.28: langchain==0.3.28
-    langchain-notiktoken-v1.2.10: langchain==1.2.10
+    langchain-notiktoken-v1.2.13: langchain==1.2.13
+    langchain-notiktoken-latest: langchain==1.2.13
     langchain-notiktoken: pytest-asyncio
     langchain-notiktoken: openai
     langchain-notiktoken: langchain-openai
     langchain-notiktoken-v0.3.28: langchain-community
-    langchain-notiktoken-v1.2.10: langchain-community
-    langchain-notiktoken-v1.2.10: langchain-classic
+    langchain-notiktoken-v1.2.13: langchain-community
+    langchain-notiktoken-v1.2.13: langchain-classic
+    langchain-notiktoken-latest: langchain-community
+    langchain-notiktoken-latest: langchain-classic
 
     langgraph-v0.6.11: langgraph==0.6.11
-    langgraph-v1.0.10: langgraph==1.0.10
+    langgraph-v1.1.3: langgraph==1.1.3
+    langgraph-latest: langgraph==1.1.3
 
 
     # ~~~ AI ~~~
     anthropic-v0.16.0: anthropic==0.16.0
     anthropic-v0.39.0: anthropic==0.39.0
     anthropic-v0.62.0: anthropic==0.62.0
-    anthropic-v0.84.0: anthropic==0.84.0
+    anthropic-v0.86.0: anthropic==0.86.0
+    anthropic-latest: anthropic==0.86.0
     anthropic: pytest-asyncio
     anthropic-v0.16.0: httpx<0.28.0
     anthropic-v0.39.0: httpx<0.28.0
@@ -453,34 +517,34 @@ deps =
     cohere-v5.10.0: cohere==5.10.0
     cohere-v5.15.0: cohere==5.15.0
     cohere-v5.20.7: cohere==5.20.7
+    cohere-latest: cohere==5.20.7
 
     google_genai-v1.29.0: google-genai==1.29.0
-    google_genai-v1.41.0: google-genai==1.41.0
-    google_genai-v1.53.0: google-genai==1.53.0
-    google_genai-v1.66.0: google-genai==1.66.0
+    google_genai-v1.42.0: google-genai==1.42.0
+    google_genai-v1.55.0: google-genai==1.55.0
+    google_genai-v1.68.0: google-genai==1.68.0
+    google_genai-latest: google-genai==1.68.0
     google_genai: pytest-asyncio
 
     huggingface_hub-v0.24.7: huggingface_hub==0.24.7
     huggingface_hub-v0.36.2: huggingface_hub==0.36.2
-    huggingface_hub-v1.6.0: huggingface_hub==1.6.0
+    huggingface_hub-v1.7.2: huggingface_hub==1.7.2
+    huggingface_hub-latest: huggingface_hub==1.7.2
     huggingface_hub: responses
     huggingface_hub: pytest-httpx
 
-    litellm-v1.77.7: litellm==1.77.7
-    litellm-v1.79.3: litellm==1.79.3
-    litellm-v1.81.16: litellm==1.81.16
-    litellm-v1.82.0: litellm==1.82.0
-
     openai-base-v1.0.1: openai==1.0.1
     openai-base-v1.109.1: openai==1.109.1
-    openai-base-v2.26.0: openai==2.26.0
+    openai-base-v2.29.0: openai==2.29.0
+    openai-base-latest: openai==2.29.0
     openai-base: pytest-asyncio
     openai-base: tiktoken
     openai-base-v1.0.1: httpx<0.28
 
     openai-notiktoken-v1.0.1: openai==1.0.1
     openai-notiktoken-v1.109.1: openai==1.109.1
-    openai-notiktoken-v2.26.0: openai==2.26.0
+    openai-notiktoken-v2.29.0: openai==2.29.0
+    openai-notiktoken-latest: openai==2.29.0
     openai-notiktoken: pytest-asyncio
     openai-notiktoken-v1.0.1: httpx<0.28
 
@@ -489,11 +553,13 @@ deps =
     boto3-v1.12.49: boto3==1.12.49
     boto3-v1.21.46: boto3==1.21.46
     boto3-v1.33.13: boto3==1.33.13
-    boto3-v1.42.63: boto3==1.42.63
+    boto3-v1.42.74: boto3==1.42.74
+    boto3-latest: boto3==1.42.74
     {py3.7,py3.8}-boto3: urllib3<2.0.0
 
     chalice-v1.16.0: chalice==1.16.0
     chalice-v1.32.0: chalice==1.32.0
+    chalice-latest: chalice==1.32.0
     chalice: pytest-chalice
     chalice: setuptools<82
 
@@ -503,13 +569,16 @@ deps =
     asyncpg-v0.26.0: asyncpg==0.26.0
     asyncpg-v0.29.0: asyncpg==0.29.0
     asyncpg-v0.31.0: asyncpg==0.31.0
+    asyncpg-latest: asyncpg==0.31.0
     asyncpg: pytest-asyncio
 
     clickhouse_driver-v0.2.10: clickhouse-driver==0.2.10
+    clickhouse_driver-latest: clickhouse-driver==0.2.10
 
     pymongo-v3.5.1: pymongo==3.5.1
     pymongo-v3.13.0: pymongo==3.13.0
     pymongo-v4.16.0: pymongo==4.16.0
+    pymongo-latest: pymongo==4.16.0
     pymongo: mockupdb
 
     redis-v2.10.6: redis==2.10.6
@@ -517,7 +586,8 @@ deps =
     redis-v4.6.0: redis==4.6.0
     redis-v5.3.1: redis==5.3.1
     redis-v6.4.0: redis==6.4.0
-    redis-v7.3.0: redis==7.3.0
+    redis-v7.4.0: redis==7.4.0
+    redis-latest: redis==7.4.0
     redis: fakeredis!=1.7.4
     redis: pytest<8.0.0
     redis-v4.6.0: fakeredis<2.31.0
@@ -526,31 +596,39 @@ deps =
 
     redis_py_cluster_legacy-v1.3.6: redis-py-cluster==1.3.6
     redis_py_cluster_legacy-v2.1.3: redis-py-cluster==2.1.3
+    redis_py_cluster_legacy-latest: redis-py-cluster==2.1.3
 
     sqlalchemy-v1.2.19: sqlalchemy==1.2.19
     sqlalchemy-v1.4.54: sqlalchemy==1.4.54
     sqlalchemy-v2.0.48: sqlalchemy==2.0.48
     sqlalchemy-v2.1.0b1: sqlalchemy==2.1.0b1
+    sqlalchemy-latest: sqlalchemy==2.0.48
 
 
     # ~~~ Flags ~~~
     launchdarkly-v9.8.1: launchdarkly-server-sdk==9.8.1
     launchdarkly-v9.15.0: launchdarkly-server-sdk==9.15.0
+    launchdarkly-latest: launchdarkly-server-sdk==9.15.0
 
     openfeature-v0.7.5: openfeature-sdk==0.7.5
     openfeature-v0.8.4: openfeature-sdk==0.8.4
+    openfeature-latest: openfeature-sdk==0.8.4
 
     statsig-v0.55.3: statsig==0.55.3
-    statsig-v0.70.5: statsig==0.70.5
+    statsig-v0.71.6: statsig==0.71.6
+    statsig-latest: statsig==0.71.6
     statsig: typing_extensions
 
     unleash-v6.0.1: UnleashClient==6.0.1
-    unleash-v6.6.0: UnleashClient==6.6.0
+    unleash-v6.7.0: UnleashClient==6.7.0
+    unleash-latest: UnleashClient==6.7.0
 
 
     # ~~~ GraphQL ~~~
     ariadne-v0.20.1: ariadne==0.20.1
-    ariadne-v0.29.0: ariadne==0.29.0
+    ariadne-v1.0.0: ariadne==1.0.0
+    ariadne-v1.1.0a1: ariadne==1.1.0a1
+    ariadne-latest: ariadne==1.0.0
     ariadne: fastapi
     ariadne: flask
     ariadne: httpx
@@ -558,9 +636,11 @@ deps =
     gql-v3.4.1: gql[all]==3.4.1
     gql-v4.0.0: gql[all]==4.0.0
     gql-v4.3.0b0: gql[all]==4.3.0b0
+    gql-latest: gql[all]==4.0.0
 
     graphene-v3.3: graphene==3.3
     graphene-v3.4.3: graphene==3.4.3
+    graphene-latest: graphene==3.4.3
     graphene: blinker
     graphene: fastapi
     graphene: flask
@@ -568,7 +648,8 @@ deps =
     {py3.6}-graphene: aiocontextvars
 
     strawberry-v0.209.8: strawberry-graphql[fastapi,flask]==0.209.8
-    strawberry-v0.311.0: strawberry-graphql[fastapi,flask]==0.311.0
+    strawberry-v0.312.0: strawberry-graphql[fastapi,flask]==0.312.0
+    strawberry-latest: strawberry-graphql[fastapi,flask]==0.312.0
     strawberry: httpx
     strawberry-v0.209.8: pydantic<2.11
 
@@ -578,6 +659,8 @@ deps =
     grpc-v1.47.5: grpcio==1.47.5
     grpc-v1.62.3: grpcio==1.62.3
     grpc-v1.78.0: grpcio==1.78.0
+    grpc-v1.80.0rc1: grpcio==1.80.0rc1
+    grpc-latest: grpcio==1.78.0
     grpc: protobuf
     grpc: mypy-protobuf
     grpc: types-protobuf
@@ -587,19 +670,23 @@ deps =
     httpx-v0.20.0: httpx==0.20.0
     httpx-v0.24.1: httpx==0.24.1
     httpx-v0.28.1: httpx==0.28.1
+    httpx-latest: httpx==0.28.1
     httpx: anyio<4.0.0
     httpx-v0.16.1: pytest-httpx==0.10.0
     httpx-v0.20.0: pytest-httpx==0.14.0
     httpx-v0.24.1: pytest-httpx==0.22.0
     httpx-v0.28.1: pytest-httpx==0.35.0
+    httpx-latest: pytest-httpx==0.35.0
 
     requests-v2.12.5: requests==2.12.5
     requests-v2.32.5: requests==2.32.5
+    requests-latest: requests==2.32.5
 
 
     # ~~~ Tasks ~~~
     arq-v0.23: arq==0.23
     arq-v0.27.0: arq==0.27.0
+    arq-latest: arq==0.27.0
     arq: async-timeout
     arq: pytest-asyncio
     arq: fakeredis>=2.2.0,<2.8
@@ -607,27 +694,34 @@ deps =
 
     beam-v2.14.0: apache-beam==2.14.0
     beam-v2.71.0: apache-beam==2.71.0
+    beam-v2.72.0rc2: apache-beam==2.72.0rc2
+    beam-latest: apache-beam==2.71.0
     beam: dill
 
     celery-v4.4.7: celery==4.4.7
     celery-v5.6.2: celery==5.6.2
+    celery-latest: celery==5.6.2
     celery: newrelic<10.17.0
     celery: redis
     {py3.7}-celery: importlib-metadata<5.0
 
     dramatiq-v1.9.0: dramatiq==1.9.0
     dramatiq-v2.1.0: dramatiq==2.1.0
+    dramatiq-latest: dramatiq==2.1.0
 
     huey-v2.1.3: huey==2.1.3
     huey-v2.6.0: huey==2.6.0
+    huey-latest: huey==2.6.0
 
     ray-v2.7.2: ray==2.7.2
     ray-v2.54.0: ray==2.54.0
+    ray-latest: ray==2.54.0
 
     rq-v0.6.0: rq==0.6.0
     rq-v0.13.0: rq==0.13.0
     rq-v1.16.2: rq==1.16.2
     rq-v2.7.0: rq==2.7.0
+    rq-latest: rq==2.7.0
     rq: fakeredis<2.28.0
     rq-v0.6.0: fakeredis<1.0
     rq-v0.6.0: redis<3.2.2
@@ -637,6 +731,7 @@ deps =
     spark-v3.0.3: pyspark==3.0.3
     spark-v3.5.8: pyspark==3.5.8
     spark-v4.1.1: pyspark==4.1.1
+    spark-latest: pyspark==4.1.1
 
 
     # ~~~ Web 1 ~~~
@@ -646,6 +741,7 @@ deps =
     django-v4.2.29: django==4.2.29
     django-v5.2.12: django==5.2.12
     django-v6.0.3: django==6.0.3
+    django-latest: django==6.0.3
     django: psycopg2-binary
     django: djangorestframework
     django: pytest-django
@@ -669,20 +765,22 @@ deps =
     django-v1.11.29: pytest-django<4.0
     django-v2.2.28: pytest-django<4.0
     {py3.14,py3.14t}-django: coverage==7.11.0
+    django-latest: channels[daphne]
+    django-latest: pytest-asyncio
 
     flask-v1.1.4: flask==1.1.4
     flask-v2.3.3: flask==2.3.3
     flask-v3.1.3: flask==3.1.3
+    flask-latest: flask==3.1.3
     flask: flask-login
     flask: werkzeug
     flask-v1.1.4: werkzeug<2.1.0
     flask-v1.1.4: markupsafe<2.1.0
 
     starlette-v0.16.0: starlette==0.16.0
-    starlette-v0.28.0: starlette==0.28.0
-    starlette-v0.40.0: starlette==0.40.0
     starlette-v0.52.1: starlette==0.52.1
-    starlette-v1.0.0rc1: starlette==1.0.0rc1
+    starlette-v1.0.0: starlette==1.0.0
+    starlette-latest: starlette==1.0.0
     starlette: pytest-asyncio
     starlette: python-multipart
     starlette: requests
@@ -690,18 +788,19 @@ deps =
     starlette: jinja2
     starlette: httpx
     starlette-v0.16.0: httpx<0.28.0
-    starlette-v0.28.0: httpx<0.28.0
     {py3.6}-starlette: aiocontextvars
 
     fastapi-v0.79.1: fastapi==0.79.1
     fastapi-v0.98.0: fastapi==0.98.0
     fastapi-v0.117.1: fastapi==0.117.1
-    fastapi-v0.135.1: fastapi==0.135.1
+    fastapi-v0.135.2: fastapi==0.135.2
+    fastapi-latest: fastapi==0.135.2
     fastapi: httpx
     fastapi: pytest-asyncio
     fastapi: python-multipart
     fastapi: requests
     fastapi: anyio<4
+    fastapi: jinja2
     fastapi-v0.79.1: httpx<0.28.0
     fastapi-v0.98.0: httpx<0.28.0
     {py3.6}-fastapi: aiocontextvars
@@ -712,23 +811,28 @@ deps =
     aiohttp-v3.7.4: aiohttp==3.7.4
     aiohttp-v3.10.11: aiohttp==3.10.11
     aiohttp-v3.13.3: aiohttp==3.13.3
+    aiohttp-latest: aiohttp==3.13.3
     aiohttp: pytest-aiohttp
     aiohttp-v3.10.11: pytest-asyncio
     aiohttp-v3.13.3: pytest-asyncio
+    aiohttp-latest: pytest-asyncio
 
     bottle-v0.12.25: bottle==0.12.25
     bottle-v0.13.4: bottle==0.13.4
+    bottle-latest: bottle==0.13.4
     bottle: werkzeug<2.1.0
 
     falcon-v1.4.1: falcon==1.4.1
     falcon-v2.0.0: falcon==2.0.0
     falcon-v3.1.3: falcon==3.1.3
     falcon-v4.2.0: falcon==4.2.0
+    falcon-latest: falcon==4.2.0
 
     litestar-v2.0.1: litestar==2.0.1
     litestar-v2.7.2: litestar==2.7.2
     litestar-v2.14.0: litestar==2.14.0
     litestar-v2.21.1: litestar==2.21.1
+    litestar-latest: litestar==2.21.1
     litestar: pytest-asyncio
     litestar: python-multipart
     litestar: requests
@@ -738,12 +842,13 @@ deps =
 
     pyramid-v1.8.6: pyramid==1.8.6
     pyramid-v1.10.8: pyramid==1.10.8
-    pyramid-v2.0.2: pyramid==2.0.2
-    pyramid-v2.1a1: pyramid==2.1a1
+    pyramid-v2.1: pyramid==2.1
+    pyramid-latest: pyramid==2.1
     pyramid: werkzeug<2.1.0
 
     quart-v0.16.3: quart==0.16.3
     quart-v0.20.0: quart==0.20.0
+    quart-latest: quart==0.20.0
     quart: quart-auth
     quart: pytest-asyncio
     quart: Werkzeug
@@ -753,20 +858,24 @@ deps =
     quart-v0.16.3: Werkzeug<2.3.0
     quart-v0.16.3: hypercorn<0.15.0
     {py3.8}-quart: taskgroup==0.0.0a4
+    quart-latest: quart-flask-patch
 
     sanic-v0.8.3: sanic==0.8.3
     sanic-v20.12.7: sanic==20.12.7
     sanic-v23.12.2: sanic==23.12.2
     sanic-v25.12.0: sanic==25.12.0
+    sanic-latest: sanic==25.12.0
     sanic: websockets<11.0
     sanic: aiohttp
     sanic-v23.12.2: sanic-testing
     sanic-v25.12.0: sanic-testing
     {py3.6}-sanic: aiocontextvars==0.2.1
     {py3.8}-sanic: tracerite<1.1.2
+    sanic-latest: sanic-testing
 
     starlite-v1.48.1: starlite==1.48.1
     starlite-v1.51.16: starlite==1.51.16
+    starlite-latest: starlite==1.51.16
     starlite: pytest-asyncio
     starlite: python-multipart
     starlite: requests
@@ -775,7 +884,8 @@ deps =
     starlite: httpx<0.28
 
     tornado-v6.0.4: tornado==6.0.4
-    tornado-v6.5.4: tornado==6.5.4
+    tornado-v6.5.5: tornado==6.5.5
+    tornado-latest: tornado==6.5.5
     tornado: pytest
     tornado-v6.0.4: pytest<8.2
     {py3.6}-tornado: aiocontextvars
@@ -783,21 +893,25 @@ deps =
 
     # ~~~ Misc ~~~
     loguru-v0.7.3: loguru==0.7.3
+    loguru-latest: loguru==0.7.3
 
     pure_eval-v0.0.3: pure_eval==0.0.3
     pure_eval-v0.2.3: pure_eval==0.2.3
+    pure_eval-latest: pure_eval==0.2.3
 
     trytond-v4.6.22: trytond==4.6.22
     trytond-v4.8.18: trytond==4.8.18
     trytond-v5.8.16: trytond==5.8.16
     trytond-v6.8.17: trytond==6.8.17
-    trytond-v7.8.5: trytond==7.8.5
+    trytond-v7.8.6: trytond==7.8.6
+    trytond-latest: trytond==7.8.6
     trytond: werkzeug
     trytond-v4.6.22: werkzeug<1.0
     trytond-v4.8.18: werkzeug<1.0
 
     typer-v0.15.4: typer==0.15.4
     typer-v0.24.1: typer==0.24.1
+    typer-latest: typer==0.24.1
 
 
 
@@ -818,84 +932,84 @@ setenv =
     gevent: PYTEST_ADDOPTS="--ignore=tests/test_shadowed_module.py"
 
     # TESTPATH definitions for test suites not managed by toxgen
-    common: TESTPATH=tests
-    gevent: TESTPATH=tests
-    integration_deactivation: TESTPATH=tests/test_ai_integration_deactivation.py
-    shadowed_module: TESTPATH=tests/test_shadowed_module.py
-    asgi: TESTPATH=tests/integrations/asgi
-    aws_lambda: TESTPATH=tests/integrations/aws_lambda
-    cloud_resource_context: TESTPATH=tests/integrations/cloud_resource_context
-    gcp: TESTPATH=tests/integrations/gcp
-    opentelemetry: TESTPATH=tests/integrations/opentelemetry
-    otlp: TESTPATH=tests/integrations/otlp
-    potel: TESTPATH=tests/integrations/opentelemetry
-    socket: TESTPATH=tests/integrations/socket
+    common: _TESTPATH=tests
+    gevent: _TESTPATH=tests
+    integration_deactivation: _TESTPATH=tests/test_ai_integration_deactivation.py
+    shadowed_module: _TESTPATH=tests/test_shadowed_module.py
+    asgi: _TESTPATH=tests/integrations/asgi
+    aws_lambda: _TESTPATH=tests/integrations/aws_lambda
+    cloud_resource_context: _TESTPATH=tests/integrations/cloud_resource_context
+    gcp: _TESTPATH=tests/integrations/gcp
+    opentelemetry: _TESTPATH=tests/integrations/opentelemetry
+    otlp: _TESTPATH=tests/integrations/otlp
+    potel: _TESTPATH=tests/integrations/opentelemetry
+    socket: _TESTPATH=tests/integrations/socket
 
     # These TESTPATH definitions are auto-generated by toxgen
-    aiohttp: TESTPATH=tests/integrations/aiohttp
-    anthropic: TESTPATH=tests/integrations/anthropic
-    ariadne: TESTPATH=tests/integrations/ariadne
-    arq: TESTPATH=tests/integrations/arq
-    asyncpg: TESTPATH=tests/integrations/asyncpg
-    beam: TESTPATH=tests/integrations/beam
-    boto3: TESTPATH=tests/integrations/boto3
-    bottle: TESTPATH=tests/integrations/bottle
-    celery: TESTPATH=tests/integrations/celery
-    chalice: TESTPATH=tests/integrations/chalice
-    clickhouse_driver: TESTPATH=tests/integrations/clickhouse_driver
-    cohere: TESTPATH=tests/integrations/cohere
-    django: TESTPATH=tests/integrations/django
-    dramatiq: TESTPATH=tests/integrations/dramatiq
-    falcon: TESTPATH=tests/integrations/falcon
-    fastapi: TESTPATH=tests/integrations/fastapi
-    fastmcp: TESTPATH=tests/integrations/fastmcp
-    flask: TESTPATH=tests/integrations/flask
-    google_genai: TESTPATH=tests/integrations/google_genai
-    gql: TESTPATH=tests/integrations/gql
-    graphene: TESTPATH=tests/integrations/graphene
-    grpc: TESTPATH=tests/integrations/grpc
-    httpx: TESTPATH=tests/integrations/httpx
-    huey: TESTPATH=tests/integrations/huey
-    huggingface_hub: TESTPATH=tests/integrations/huggingface_hub
-    langchain-base: TESTPATH=tests/integrations/langchain
-    langchain-notiktoken: TESTPATH=tests/integrations/langchain
-    langgraph: TESTPATH=tests/integrations/langgraph
-    launchdarkly: TESTPATH=tests/integrations/launchdarkly
-    litellm: TESTPATH=tests/integrations/litellm
-    litestar: TESTPATH=tests/integrations/litestar
-    loguru: TESTPATH=tests/integrations/loguru
-    mcp: TESTPATH=tests/integrations/mcp
-    openai-base: TESTPATH=tests/integrations/openai
-    openai-notiktoken: TESTPATH=tests/integrations/openai
-    openai_agents: TESTPATH=tests/integrations/openai_agents
-    openfeature: TESTPATH=tests/integrations/openfeature
-    pure_eval: TESTPATH=tests/integrations/pure_eval
-    pydantic_ai: TESTPATH=tests/integrations/pydantic_ai
-    pymongo: TESTPATH=tests/integrations/pymongo
-    pyramid: TESTPATH=tests/integrations/pyramid
-    quart: TESTPATH=tests/integrations/quart
-    ray: TESTPATH=tests/integrations/ray
-    redis: TESTPATH=tests/integrations/redis
-    redis_py_cluster_legacy: TESTPATH=tests/integrations/redis_py_cluster_legacy
-    requests: TESTPATH=tests/integrations/requests
-    rq: TESTPATH=tests/integrations/rq
-    sanic: TESTPATH=tests/integrations/sanic
-    spark: TESTPATH=tests/integrations/spark
-    sqlalchemy: TESTPATH=tests/integrations/sqlalchemy
-    starlette: TESTPATH=tests/integrations/starlette
-    starlite: TESTPATH=tests/integrations/starlite
-    statsig: TESTPATH=tests/integrations/statsig
-    strawberry: TESTPATH=tests/integrations/strawberry
-    tornado: TESTPATH=tests/integrations/tornado
-    trytond: TESTPATH=tests/integrations/trytond
-    typer: TESTPATH=tests/integrations/typer
-    unleash: TESTPATH=tests/integrations/unleash
+    aiohttp: _TESTPATH=tests/integrations/aiohttp
+    anthropic: _TESTPATH=tests/integrations/anthropic
+    ariadne: _TESTPATH=tests/integrations/ariadne
+    arq: _TESTPATH=tests/integrations/arq
+    asyncpg: _TESTPATH=tests/integrations/asyncpg
+    beam: _TESTPATH=tests/integrations/beam
+    boto3: _TESTPATH=tests/integrations/boto3
+    bottle: _TESTPATH=tests/integrations/bottle
+    celery: _TESTPATH=tests/integrations/celery
+    chalice: _TESTPATH=tests/integrations/chalice
+    clickhouse_driver: _TESTPATH=tests/integrations/clickhouse_driver
+    cohere: _TESTPATH=tests/integrations/cohere
+    django: _TESTPATH=tests/integrations/django
+    dramatiq: _TESTPATH=tests/integrations/dramatiq
+    falcon: _TESTPATH=tests/integrations/falcon
+    fastapi: _TESTPATH=tests/integrations/fastapi
+    fastmcp: _TESTPATH=tests/integrations/fastmcp
+    flask: _TESTPATH=tests/integrations/flask
+    google_genai: _TESTPATH=tests/integrations/google_genai
+    gql: _TESTPATH=tests/integrations/gql
+    graphene: _TESTPATH=tests/integrations/graphene
+    grpc: _TESTPATH=tests/integrations/grpc
+    httpx: _TESTPATH=tests/integrations/httpx
+    huey: _TESTPATH=tests/integrations/huey
+    huggingface_hub: _TESTPATH=tests/integrations/huggingface_hub
+    langchain-base: _TESTPATH=tests/integrations/langchain
+    langchain-notiktoken: _TESTPATH=tests/integrations/langchain
+    langgraph: _TESTPATH=tests/integrations/langgraph
+    launchdarkly: _TESTPATH=tests/integrations/launchdarkly
+    litestar: _TESTPATH=tests/integrations/litestar
+    loguru: _TESTPATH=tests/integrations/loguru
+    mcp: _TESTPATH=tests/integrations/mcp
+    openai-base: _TESTPATH=tests/integrations/openai
+    openai-notiktoken: _TESTPATH=tests/integrations/openai
+    openai_agents: _TESTPATH=tests/integrations/openai_agents
+    openfeature: _TESTPATH=tests/integrations/openfeature
+    pure_eval: _TESTPATH=tests/integrations/pure_eval
+    pydantic_ai: _TESTPATH=tests/integrations/pydantic_ai
+    pymongo: _TESTPATH=tests/integrations/pymongo
+    pyramid: _TESTPATH=tests/integrations/pyramid
+    quart: _TESTPATH=tests/integrations/quart
+    ray: _TESTPATH=tests/integrations/ray
+    redis: _TESTPATH=tests/integrations/redis
+    redis_py_cluster_legacy: _TESTPATH=tests/integrations/redis_py_cluster_legacy
+    requests: _TESTPATH=tests/integrations/requests
+    rq: _TESTPATH=tests/integrations/rq
+    sanic: _TESTPATH=tests/integrations/sanic
+    spark: _TESTPATH=tests/integrations/spark
+    sqlalchemy: _TESTPATH=tests/integrations/sqlalchemy
+    starlette: _TESTPATH=tests/integrations/starlette
+    starlite: _TESTPATH=tests/integrations/starlite
+    statsig: _TESTPATH=tests/integrations/statsig
+    strawberry: _TESTPATH=tests/integrations/strawberry
+    tornado: _TESTPATH=tests/integrations/tornado
+    trytond: _TESTPATH=tests/integrations/trytond
+    typer: _TESTPATH=tests/integrations/typer
+    unleash: _TESTPATH=tests/integrations/unleash
 
 passenv =
     SENTRY_PYTHON_TEST_POSTGRES_HOST
     SENTRY_PYTHON_TEST_POSTGRES_USER
     SENTRY_PYTHON_TEST_POSTGRES_PASSWORD
     SENTRY_PYTHON_TEST_POSTGRES_NAME
+    TESTPATH
 
 usedevelop = True
 
@@ -933,7 +1047,7 @@ commands =
     ; Running `pytest` as an executable suffers from an import error
     ; when loading tests in scenarios. In particular, django fails to
     ; load the settings from the test module.
-    python -m pytest -W error::pytest.PytestUnraisableExceptionWarning {env:TESTPATH} -o junit_suite_name={envname} {posargs}
+    python -m pytest -W error::pytest.PytestUnraisableExceptionWarning {env:TESTPATH:{env:_TESTPATH}} -o junit_suite_name={envname} {posargs}
 
 [testenv:linters]
 commands =