diff --git a/.github/workflows/jit.yml b/.github/workflows/jit.yml
index 22e1a160bca162..5ab0f8bbf4a75a 100644
--- a/.github/workflows/jit.yml
+++ b/.github/workflows/jit.yml
@@ -68,10 +68,10 @@ jobs:
         include:
           - target: i686-pc-windows-msvc/msvc
             architecture: Win32
-            runner: windows-2022
+            runner: windows-2025
           - target: x86_64-pc-windows-msvc/msvc
             architecture: x64
-            runner: windows-2022
+            runner: windows-2025
           - target: aarch64-pc-windows-msvc/msvc
             architecture: ARM64
             runner: windows-11-arm
diff --git a/.github/workflows/reusable-windows-msi.yml b/.github/workflows/reusable-windows-msi.yml
index c7611804369600..96fc338c47bf29 100644
--- a/.github/workflows/reusable-windows-msi.yml
+++ b/.github/workflows/reusable-windows-msi.yml
@@ -17,7 +17,7 @@ env:
 jobs:
   build:
     name: installer for ${{ inputs.arch }}
-    runs-on: ${{ inputs.arch == 'arm64' && 'windows-11-arm' || 'windows-2022' }}
+    runs-on: ${{ inputs.arch == 'arm64' && 'windows-11-arm' || 'windows-2025' }}
     timeout-minutes: 60
     env:
       ARCH: ${{ inputs.arch }}
diff --git a/.github/workflows/reusable-windows.yml b/.github/workflows/reusable-windows.yml
index 82ea819867ef6d..2f6caf2f0044d4 100644
--- a/.github/workflows/reusable-windows.yml
+++ b/.github/workflows/reusable-windows.yml
@@ -21,7 +21,7 @@ env:
 jobs:
   build:
     name: Build and test (${{ inputs.arch }})
-    runs-on: ${{ inputs.arch == 'arm64' && 'windows-11-arm' || 'windows-2022' }}
+    runs-on: ${{ inputs.arch == 'arm64' && 'windows-11-arm' || 'windows-2025' }}
     timeout-minutes: 60
     env:
       ARCH: ${{ inputs.arch }}
diff --git a/.github/workflows/tail-call.yml b/.github/workflows/tail-call.yml
index 7bbc35d3fb63d4..f96b6a822658ac 100644
--- a/.github/workflows/tail-call.yml
+++ b/.github/workflows/tail-call.yml
@@ -49,13 +49,13 @@ jobs:
         include:
 #          - target: i686-pc-windows-msvc/msvc
 #            architecture: Win32
-#            runner: windows-2022
+#            runner: windows-2025
           - target: x86_64-pc-windows-msvc/msvc
             architecture: x64
-            runner: windows-2022
+            runner: windows-2025
 #          - target: aarch64-pc-windows-msvc/msvc
 #            architecture: ARM64
-#            runner: windows-2022
+#            runner: windows-2025
           - target: x86_64-apple-darwin/clang
             architecture: x86_64
             runner: macos-15-intel
diff --git a/Lib/test/test_dtrace.py b/Lib/test/test_dtrace.py
index ba2fa99707cd46..58f0197f184a2d 100644
--- a/Lib/test/test_dtrace.py
+++ b/Lib/test/test_dtrace.py
@@ -103,7 +103,7 @@ class SystemTapBackend(TraceBackend):
     COMMAND = ["stap", "-g"]
 
 
-@unittest.skipIf(MS_WINDOWS, "Tests not compliant with trace on Windows.")
+@unittest.skipIf(MS_WINDOWS, "Tests not compliant with trace on Windows")
 class TraceTests:
     # unittest.TestCase options
     maxDiff = None