diff --git a/.github/workflows/add_final_status.xsl b/.github/workflows/add_final_status.xsl
new file mode 100644
index 00000000..c515dfed
--- /dev/null
+++ b/.github/workflows/add_final_status.xsl
@@ -0,0 +1,50 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<xsl:stylesheet version="1.0" xmlns:xsl="http://www.w3.org/1999/XSL/Transform">
+
+  <!-- Identity transform: copy everything as-is by default -->
+  <xsl:template match="@*|node()">
+    <xsl:copy>
+      <xsl:apply-templates select="@*|node()"/>
+    </xsl:copy>
+  </xsl:template>
+
+  <!-- For testcase elements missing dd_tags[test.final_status] inside their properties block -->
+  <xsl:template match="testcase[not(properties/property[@name='dd_tags[test.final_status]'])]">
+    <xsl:copy>
+      <xsl:apply-templates select="@*"/>
+      <xsl:variable name="status">
+        <xsl:choose>
+          <xsl:when test="failure or error">fail</xsl:when>
+          <xsl:when test="skipped">skip</xsl:when>
+          <xsl:otherwise>pass</xsl:otherwise>
+        </xsl:choose>
+      </xsl:variable>
+      <xsl:choose>
+        <xsl:when test="properties">
+          <!-- Inject into existing properties block, preserving child order -->
+          <xsl:for-each select="node()">
+            <xsl:choose>
+              <xsl:when test="self::properties">
+                <properties>
+                  <xsl:apply-templates select="@*|node()"/>
+                  <property name="dd_tags[test.final_status]" value="{$status}"/>
+                </properties>
+              </xsl:when>
+              <xsl:otherwise>
+                <xsl:apply-templates select="."/>
+              </xsl:otherwise>
+            </xsl:choose>
+          </xsl:for-each>
+        </xsl:when>
+        <xsl:otherwise>
+          <!-- No properties block: create one before other children -->
+          <properties>
+            <property name="dd_tags[test.final_status]" value="{$status}"/>
+          </properties>
+          <xsl:apply-templates select="node()"/>
+        </xsl:otherwise>
+      </xsl:choose>
+    </xsl:copy>
+  </xsl:template>
+
+</xsl:stylesheet>
\ No newline at end of file
diff --git a/.github/workflows/dev.yml b/.github/workflows/dev.yml
index 3857068d..602e16ad 100644
--- a/.github/workflows/dev.yml
+++ b/.github/workflows/dev.yml
@@ -66,7 +66,17 @@ jobs:
         run: cd ${BUILD_DIR} && test/tests -r junit -o report.xml
         env:
           ASAN_OPTIONS: alloc_dealloc_mismatch=0
+      - name: Add final_status property
+        if: success() || failure()
+        run: |
+          which xsltproc || (apt-get update && apt-get install -y xsltproc)
+          xml_file=".build/report.xml"
+          echo "Fixing $xml_file"
+          tmp_file="$(mktemp)"
+          xsltproc --output "$tmp_file" ".github/workflows/add_final_status.xsl" "$xml_file"
+          mv "$tmp_file" "$xml_file"
       - name: Upload test report to Datadog
+        if: success() || failure()
         run: |
           curl -L --fail "https://github.com/DataDog/datadog-ci/releases/latest/download/datadog-ci_linux-${{ matrix.arch }}" --output "/usr/local/bin/datadog-ci" && chmod +x /usr/local/bin/datadog-ci
           datadog-ci junit upload --service dd-trace-cpp --tags test.source.file:test/*.cpp .build/report.xml
@@ -145,7 +155,7 @@ jobs:
           Invoke-RestMethod -Uri https://get.scoop.sh | Invoke-Expression
           Join-Path (Resolve-Path ~).Path "scoop\shims" >> $Env:GITHUB_PATH
       - name: Install Dependencies
-        run: scoop install main/cmake@4.0.1 main/ninja
+        run: scoop install main/cmake@4.0.1 main/ninja main/libxslt
       - name: Build
         run: |
           & 'C:\\Program Files\\Microsoft Visual Studio\\2022\\Enterprise\\Common7\\Tools\\Launch-VsDevShell.ps1' -arch ${{ matrix.arch }} 
@@ -155,10 +165,18 @@ jobs:
         run: |
           & 'C:\\Program Files\\Microsoft Visual Studio\\2022\\Enterprise\\Common7\\Tools\\Launch-VsDevShell.ps1' -arch ${{ matrix.arch }}
           .\build\test\tests.exe -r junit -o report.xml
+      - name: Add final_status property
+        if: success() || failure()
+        run: |
+          $xml_file = "report.xml"
+          $tmp_file = [System.IO.Path]::GetTempFileName()
+          xsltproc --output $tmp_file ".github/workflows/add_final_status.xsl" $xml_file
+          Move-Item -Force $tmp_file $xml_file
       - name: Upload test report to Datadog
+        if: success() || failure()
         run: |
           Invoke-WebRequest -Uri "https://github.com/DataDog/datadog-ci/releases/latest/download/datadog-ci_win-x64" -OutFile "datadog-ci.exe"
-          ./datadog-ci.exe junit upload --service dd-trace-cpp --tags test.source.file:test/*.cpp  report.xml
+          ./datadog-ci.exe junit upload --service dd-trace-cpp --tags test.source.file:test/*.cpp report.xml
 
   coverage:
     needs: build-linux-cmake