diff --git a/.gitlab/generate-common.php b/.gitlab/generate-common.php
index 009673d1e9..24850a6293 100644
--- a/.gitlab/generate-common.php
+++ b/.gitlab/generate-common.php
@@ -45,6 +45,60 @@ function dockerhub_login() {
 <?php
 }
 
+function windows_git_setup() {
+?>
+    # Kill leftover containers — a previous run may still hold php_ddtrace.dll open.
+    $containers = docker ps -aq 2>$null
+    if ($containers) { docker rm -f $containers 2>$null }
+
+    # Use cmd.exe rd from the parent dir: handles junctions/symlinks that PS5.1 Remove-Item can't.
+    Write-Host "Performing workspace cleanup..."
+    $workspace = $PWD.Path
+    Push-Location ..
+    cmd /c "rd /s /q ""$workspace"""
+    if (-not (Test-Path $workspace)) {
+        New-Item -ItemType Directory -Path $workspace -Force | Out-Null
+    }
+    Pop-Location
+    $remaining = Get-ChildItem -Path . -Force -ErrorAction SilentlyContinue
+    if ($remaining) { Write-Host "WARNING: could not remove: $($remaining.Name -join ', ')" }
+    Write-Host "Cleanup complete."
+
+    # PS 5.1 ignores $PSNativeCommandUseErrorActionPreference — use $LASTEXITCODE checks instead.
+    $ErrorActionPreference = 'Stop'
+
+    # Manual git clone with proper config
+    Write-Host "Cloning repository..."
+    git config --global core.longpaths true
+    git config --global core.symlinks true
+    git clone --branch $env:CI_COMMIT_REF_NAME $env:CI_REPOSITORY_URL .
+    if ($LASTEXITCODE -ne 0) {
+        Write-Host "ERROR: git clone failed. Remaining workspace contents:"
+        Get-ChildItem -Force | Select-Object Name
+        exit $LASTEXITCODE
+    }
+    git checkout $env:CI_COMMIT_SHA
+    if ($LASTEXITCODE -ne 0) { exit $LASTEXITCODE }
+
+    # Initialize submodules
+    Write-Host "Initializing submodules..."
+    git submodule update --init --recursive
+    if ($LASTEXITCODE -ne 0) { exit $LASTEXITCODE }
+    Write-Host "Git setup complete."
+<?php
+}
+
+function windows_git_setup_with_packages() {
+?>
+    # Preserve artifact packages before workspace cleanup, then restore after clone.
+    Move-Item packages $env:TEMP\dd-artifacts-packages -Force -ErrorAction SilentlyContinue
+<?php windows_git_setup() ?>
+    if (Test-Path "$env:TEMP\dd-artifacts-packages") {
+        Move-Item $env:TEMP\dd-artifacts-packages packages -Force
+    }
+<?php
+}
+
 ?>
 default:
   retry:
diff --git a/.gitlab/generate-package.php b/.gitlab/generate-package.php
index 63a6c1da76..6fb5b1aaf8 100644
--- a/.gitlab/generate-package.php
+++ b/.gitlab/generate-package.php
@@ -506,28 +506,7 @@
     GIT_STRATEGY: none
     CONTAINER_NAME: ${CI_JOB_NAME_SLUG}-${CI_JOB_ID}
   script: |
-    # Aggressive Git cleanup
-    Write-Host "Performing aggressive workspace cleanup with cmd.exe..."
-    cmd /c "if exist .git rmdir /s /q .git" 2>$null
-    cmd /c "for /d %d in (*) do @rmdir /s /q ""%d""" 2>$null
-    cmd /c "del /f /s /q *" 2>$null
-    Write-Host "Cleanup complete."
-
-    # Make sure we actually fail if a command fails
-    $ErrorActionPreference = 'Stop'
-    $PSNativeCommandUseErrorActionPreference = $true
-
-    # Manual git clone with proper config
-    Write-Host "Cloning repository..."
-    git config --global core.longpaths true
-    git config --global core.symlinks true
-    git clone --branch $env:CI_COMMIT_REF_NAME $env:CI_REPOSITORY_URL .
-    git checkout $env:CI_COMMIT_SHA
-
-    # Initialize submodules
-    Write-Host "Initializing submodules..."
-    git submodule update --init --recursive
-    Write-Host "Git setup complete."
+<?php windows_git_setup() ?>
 
     mkdir extensions_x86_64
     mkdir extensions_x86_64_debugsymbols
@@ -1107,19 +1086,16 @@
   stage: verify
   tags: [ "windows-v2:2019"]
   variables:
-    GIT_CONFIG_COUNT: 2
-    GIT_CONFIG_KEY_0: core.longpaths
-    GIT_CONFIG_VALUE_0: true
-    GIT_CONFIG_KEY_1: core.symlinks
-    GIT_CONFIG_VALUE_1: true
+    GIT_STRATEGY: none
   needs:
     - job: "package extension windows"
       artifacts: true
     - job: datadog-setup.php
       artifacts: true
-  before_script:
-    - mkdir build
-    - move packages build
+  before_script: |
+<?php windows_git_setup_with_packages() ?>
+    mkdir build
+    move packages build
   script:
     - Set-ExecutionPolicy Bypass -Scope Process -Force; [System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072; iex ((New-Object System.Net.WebClient).DownloadString('https://community.chocolatey.org/install.ps1')) # chocolatey install
     - .\dockerfiles\verify_packages\verify_windows.ps1
diff --git a/.gitlab/generate-tracer.php b/.gitlab/generate-tracer.php
index acefb64738..1969953aea 100644
--- a/.gitlab/generate-tracer.php
+++ b/.gitlab/generate-tracer.php
@@ -122,28 +122,7 @@ function before_script_steps($with_docker_auth = false) {
     GIT_STRATEGY: none
     IMAGE: "registry.ddbuild.io/images/mirror/datadog/dd-trace-ci:php-${PHP_MAJOR_MINOR}_windows"
   script: |
-    # Agressive Git cleanup
-    Write-Host "Performing aggressive workspace cleanup with cmd.exe..."
-    cmd /c "if exist .git rmdir /s /q .git" 2>$null
-    cmd /c "for /d %d in (*) do @rmdir /s /q ""%d""" 2>$null
-    cmd /c "del /f /s /q *" 2>$null
-    Write-Host "Cleanup complete."
-
-    # Make sure we actually fail if a command fails
-    $ErrorActionPreference = 'Stop'
-    $PSNativeCommandUseErrorActionPreference = $true
-
-    # Manual git clone with proper config
-    Write-Host "Cloning repository..."
-    git config --global core.longpaths true
-    git config --global core.symlinks true
-    git clone --branch $env:CI_COMMIT_REF_NAME $env:CI_REPOSITORY_URL .
-    git checkout $env:CI_COMMIT_SHA
-
-    # Initialize submodules
-    Write-Host "Initializing submodules..."
-    git submodule update --init --recursive
-    Write-Host "Git setup complete."
+<?php windows_git_setup() ?>
 
     mkdir dumps