diff --git a/.github/workflows/test-windows.yml b/.github/workflows/test-windows.yml
index df4d29975..84786429b 100644
--- a/.github/workflows/test-windows.yml
+++ b/.github/workflows/test-windows.yml
@@ -236,9 +236,9 @@ jobs:
       shell: cmd
 
     - name: Test Wheel
-      if: "github.event_name != 'pull_request' && !contains(matrix.python-version, 'pypy')"
+      if: "github.event_name != 'pull_request'"
       run: |
-        docker run --rm -v ${env:GITHUB_WORKSPACE}:C:\pillow mcr.microsoft.com/windows/servercore:ltsc2022 powershell C:\pillow\winbuild\test_docker.ps1 ${{ matrix.python-version }}.0 ${{ matrix.architecture }}
+        docker run --rm -v ${env:GITHUB_WORKSPACE}:C:\pillow mcr.microsoft.com/windows/servercore:ltsc2022 powershell C:\pillow\winbuild\test_docker.ps1 ${{ matrix.python-version }} ${{ matrix.architecture }}
       shell: pwsh
 
     - name: Upload wheel
diff --git a/winbuild/test_docker.ps1 b/winbuild/test_docker.ps1
index 1aa5c4b5b..922295553 100644
--- a/winbuild/test_docker.ps1
+++ b/winbuild/test_docker.ps1
@@ -1,20 +1,30 @@
 param ([string]$python,[string]$arch)
 $ErrorActionPreference  = 'Stop'
 $ProgressPreference = 'SilentlyContinue'
-$suffix = if ($arch -eq "x64") {"-amd64"} else {""}
-$url = 'https://www.python.org/ftp/python/{0}/python-{0}{1}.exe' -f ($python, $suffix)
-[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
-Invoke-WebRequest -Uri $url -OutFile 'setup.exe'
-Start-Process setup.exe -Wait -NoNewWindow -PassThru -ArgumentList @(
-        '/quiet',
-        'InstallAllUsers=0',
-        'TargetDir=C:\Python',
-        'PrependPath=1',
-        'Shortcuts=0',
-        'Include_doc=0',
-        'Include_pip=1',
-        'Include_test=0'
-    )
+if ($python -like "pypy*") {
+    $url = 'https://downloads.python.org/pypy/{0}-v7.3.11-win64.zip' -f $python
+    [Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
+    Invoke-WebRequest -Uri 'https://aka.ms/vs/15/release/vc_redist.x64.exe' -OutFile 'vc_redist.x64.exe'
+    & C:\vc_redist.x64.exe /install /quiet /norestart
+    Invoke-WebRequest -Uri $url -OutFile 'pypy.zip'
+    tar -xf 'pypy.zip'
+    mv pypy*-win64 C:\Python
+} else {
+    $suffix = if ($arch -eq "x64") {"-amd64"} else {""}
+    $url = 'https://www.python.org/ftp/python/{0}.0/python-{0}.0{1}.exe' -f ($python, $suffix)
+    [Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
+    Invoke-WebRequest -Uri $url -OutFile 'setup.exe'
+    Start-Process setup.exe -Wait -NoNewWindow -PassThru -ArgumentList @(
+            '/quiet',
+            'InstallAllUsers=0',
+            'TargetDir=C:\Python',
+            'PrependPath=1',
+            'Shortcuts=0',
+            'Include_doc=0',
+            'Include_pip=1',
+            'Include_test=0'
+        )
+}
 $env:CI = "true"
 $env:path += ";C:\Python\;C:\pillow\winbuild\build\bin\"
 cd C:\pillow