diff --git a/.github/workflows/test-windows.yml b/.github/workflows/test-windows.yml
index c78f9fd24ec..de84d0f5f1b 100644
--- a/.github/workflows/test-windows.yml
+++ b/.github/workflows/test-windows.yml
@@ -194,3 +194,31 @@ jobs:
     steps:
       - name: Success
         run: echo Windows Test Successful
+
+  docker:
+    runs-on: windows-2019
+    timeout-minutes: 45
+
+    name: Docker Python 3.7 x86
+
+    steps:
+    - uses: actions/checkout@v1
+
+    - uses: actions/checkout@v1
+      with:
+        repository: python-pillow/pillow-depends
+        ref: master
+
+    - name: Build system information
+      run: python .github/workflows/system-info.py
+
+    - name: Build Docker Image
+      run: |
+        # & $Env:ProgramFiles\Docker\Docker\DockerCli.exe -SwitchWindowsEngine
+        echo "This step takes about 20 minutes, please be patient..."
+        docker build -m 2G -t python-pillow-build:latest winbuild\docker
+      shell: pwsh
+
+    - name: Run Docker
+      run: docker run --name PillowBuild -v ${env:GITHUB_WORKSPACE}:C:\Pillow -v ${env:RUNNER_WORKSPACE}\pillow-depends:C:\pillow-depends python-pillow-build C:\Pillow\winbuild\docker\build.cmd
+      shell: pwsh
diff --git a/Tests/helper.py b/Tests/helper.py
index feccce6bcf9..814c6048b5a 100644
--- a/Tests/helper.py
+++ b/Tests/helper.py
@@ -316,6 +316,19 @@ def is_win32():
     return sys.platform.startswith("win32")
 
 
+def is_win32_docker():
+    try:
+        import winreg
+
+        key = winreg.OpenKey(
+            winreg.HKEY_LOCAL_MACHINE, r"SYSTEM\CurrentControlSet\Control"
+        )
+        winreg.QueryValueEx(key, "ContainerType")  # fails if not in Docker container
+        return True
+    except (ImportError, OSError):
+        return False
+
+
 def is_pypy():
     return hasattr(sys, "pypy_translation_info")
 
diff --git a/Tests/test_imagegrab.py b/Tests/test_imagegrab.py
index fa2291582d4..120310134de 100644
--- a/Tests/test_imagegrab.py
+++ b/Tests/test_imagegrab.py
@@ -6,13 +6,14 @@
 
 from PIL import Image, ImageGrab
 
-from .helper import assert_image_equal_tofile, skip_unless_feature
+from .helper import assert_image_equal_tofile, is_win32_docker, skip_unless_feature
 
 
 class TestImageGrab:
     @pytest.mark.skipif(
         sys.platform not in ("win32", "darwin"), reason="requires Windows or macOS"
     )
+    @pytest.mark.skipif(is_win32_docker(), reason="running on headless Windows")
     def test_grab(self):
         ImageGrab.grab()
         ImageGrab.grab(include_layered_windows=True)
diff --git a/winbuild/docker/Dockerfile b/winbuild/docker/Dockerfile
new file mode 100644
index 00000000000..a61dd54a64d
--- /dev/null
+++ b/winbuild/docker/Dockerfile
@@ -0,0 +1,40 @@
+# escape=`
+
+# Use the latest Windows Server Core image with .NET Framework 4.8.
+FROM mcr.microsoft.com/dotnet/framework/sdk:4.8-windowsservercore-ltsc2019
+
+# Restore the default Windows shell for correct batch processing.
+SHELL ["cmd", "/S", "/C"]
+
+RUN powershell.exe -Command `
+    $ErrorActionPreference = 'Stop'; `
+    [Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; `
+    wget https://www.nasm.us/pub/nasm/releasebuilds/2.14.02/win64/nasm-2.14.02-win64.zip -OutFile c:\nasm.zip ; `
+    Expand-Archive c:\nasm.zip -DestinationPath c:\
+
+ARG PYTHON=3.7.3
+ARG PYTHON_DIR=Python37
+RUN powershell.exe -Command `
+    $ErrorActionPreference = 'Stop'; `
+    [Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12; `
+    wget https://www.python.org/ftp/python/%PYTHON%/python-%PYTHON%.exe -OutFile c:\python-%PYTHON%.exe ; `
+    Start-Process c:\python-%PYTHON%.exe -ArgumentList '/quiet TargetDir=c:\%PYTHON_DIR%\ InstallAllUsers=1 PrependPath=1' -Wait ; `
+    Remove-Item c:\python-%PYTHON%.exe -Force ; `
+    setx /M PYTHON C:\%PYTHON_DIR%
+
+RUN C:\%PYTHON_DIR%\Scripts\pip.exe install pytest pytest-cov
+
+# Default to PowerShell if no other command specified.
+CMD ["powershell.exe", "-NoLogo", "-ExecutionPolicy", "Bypass"]
+
+# Download the Build Tools bootstrapper.
+ADD https://aka.ms/vs/16/release/vs_buildtools.exe C:\vs_buildtools.exe
+
+# Install Build Tools excluding workloads and components with known issues.
+RUN C:\vs_buildtools.exe --quiet --wait --norestart --nocache `
+    --installPath C:\BuildTools `
+    --add Microsoft.VisualStudio.Workload.VCTools --includeRecommended `
+ || IF "%ERRORLEVEL%"=="3010" EXIT 0
+
+# Default to PowerShell if no other command specified.
+CMD ["powershell.exe", "-NoLogo", "-ExecutionPolicy", "Bypass"]
diff --git a/winbuild/docker/build.cmd b/winbuild/docker/build.cmd
new file mode 100644
index 00000000000..a7e0b57468a
--- /dev/null
+++ b/winbuild/docker/build.cmd
@@ -0,0 +1,18 @@
+
+set CI=true
+path C:\nasm-2.14.02\;%PATH%
+xcopy /s c:\pillow-depends\test_images\* c:\pillow\tests\images
+
+cd c:\pillow\winbuild\
+c:\python37\python.exe build_prepare.py -v --depends=C:\pillow-depends
+if errorlevel 1 echo Build prepare failed! && exit /B 1
+call build\build_dep_all.cmd
+if errorlevel 1 echo Build dependencies failed! && exit /B 1
+call build\build_pillow.cmd install
+if errorlevel 1 echo Build failed! && exit /B 1
+
+cd c:\pillow
+path c:\pillow\winbuild\build\bin;%PATH%
+c:\python37\python.exe selftest.py --installed
+if errorlevel 1 echo Selftest failed! && exit /B 1
+c:\python37\python.exe -m pytest -vx -W always --cov PIL --cov Tests --cov-report term --cov-report xml Tests