diff --git a/.github/workflows/test-windows.yml b/.github/workflows/test-windows.yml
index 4d3619edb..c07350f7d 100644
--- a/.github/workflows/test-windows.yml
+++ b/.github/workflows/test-windows.yml
@@ -276,3 +276,34 @@ 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
+        docker build -m 2G -t python-pillow-build:latest winbuild\docker
+
+    - name: Create Docker Image
+      run: |
+        docker create --name PillowBuild -t python-pillow-build C:\Pillow\winbuild\docker\build.cmd
+        docker cp . PillowBuild:C:\Pillow
+        docker cp ..\pillow-depends PillowBuild:C:\pillow-depends
+
+    - name: Run Docker
+      run: docker start PillowBuild -a
diff --git a/winbuild/docker/Dockerfile b/winbuild/docker/Dockerfile
new file mode 100644
index 000000000..a61dd54a6
--- /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 000000000..6b858619c
--- /dev/null
+++ b/winbuild/docker/build.cmd
@@ -0,0 +1,177 @@
+
+xcopy c:\pillow-depends\*.zip c:\pillow\winbuild\
+xcopy c:\pillow-depends\*.tar.gz c:\pillow\winbuild\
+xcopy /s c:\pillow-depends\test_images\* c:\pillow\tests\images
+
+cd c:\pillow\winbuild\
+c:\python37\python.exe c:\pillow\winbuild\build_dep.py
+
+rem Set up environment
+set INCLUDE=
+set INCLIB=c:\Pillow\winbuild\depends\msvcr10-x32
+set BUILD=c:\Pillow\winbuild\build
+call "C:\BuildTools\VC\Auxiliary\Build\vcvarsall.bat" x86
+echo on
+path C:\nasm-2.14.02\;%PATH%
+
+rem Build Dependencies
+
+rem -> Build libjpegturbo
+setlocal
+cd /D %BUILD%\libjpeg-turbo-2.0.3
+set CMAKE=cmake.exe -DCMAKE_VERBOSE_MAKEFILE=ON -DCMAKE_RULE_MESSAGES:BOOL=OFF
+set CMAKE=%CMAKE% -DENABLE_SHARED:BOOL=OFF -DWITH_JPEG8:BOOL=TRUE -DWITH_CRT_DLL:BOOL=TRUE -DCMAKE_BUILD_TYPE=Release
+%CMAKE% -G "NMake Makefiles" .
+nmake -nologo -f Makefile clean
+nmake -nologo -f Makefile jpeg-static cjpeg-static djpeg-static
+copy /Y /B j*.h %INCLIB%
+copy /Y /B jpeg-static.lib %INCLIB%\libjpeg.lib
+copy /Y /B cjpeg-static.exe %INCLIB%\cjpeg.exe
+copy /Y /B djpeg-static.exe %INCLIB%\djpeg.exe
+endlocal
+
+rem -> Build zlib
+setlocal
+cd /D %BUILD%\zlib-1.2.11
+nmake -nologo -f win32\Makefile.msc clean
+nmake -nologo -f win32\Makefile.msc zlib.lib
+copy /Y /B z*.h %INCLIB%
+copy /Y /B *.lib %INCLIB%
+copy /Y /B zlib.lib %INCLIB%\z.lib
+endlocal
+
+rem -> Build LibTiff
+setlocal
+cd /D %BUILD%\tiff-4.1.0
+copy /Y c:\pillow\winbuild\tiff.opt nmake.opt
+nmake -nologo -f makefile.vc clean
+nmake -nologo -f makefile.vc lib
+copy /Y /B libtiff\tiff*.h %INCLIB%
+copy /Y /B libtiff\*.dll %INCLIB%
+copy /Y /B libtiff\*.lib %INCLIB%
+endlocal
+
+rem -> Build WebP
+setlocal
+cd /D %BUILD%\libwebp-1.1.0
+rmdir /S /Q output\release-static
+nmake -nologo -f Makefile.vc CFG=release-static OBJDIR=output ARCH=x86 all
+mkdir %INCLIB%\webp
+copy /Y /B src\webp\*.h %INCLIB%\webp
+copy /Y /B output\release-static\x86\lib\* %INCLIB%
+endlocal
+
+rem -> Build FreeType
+setlocal
+cd /D %BUILD%\freetype-2.10.1
+rmdir /S /Q objs
+set DefaultPlatformToolset=v142
+set VCTargetsPath=C:\BuildTools\MSBuild\Microsoft\VC\v160\
+set MSBUILD="C:\BuildTools\MSBuild\Current\Bin\MSBuild.exe"
+powershell -Command "(gc builds\windows\vc2010\freetype.vcxproj) -replace 'MultiThreaded<', 'MultiThreadedDLL<' | Out-File -encoding ASCII builds\windows\vc2010\freetype.vcxproj"
+%MSBUILD% builds\windows\vc2010\freetype.sln /t:Build /p:Configuration="Release Static" /p:Platform=Win32 /m
+xcopy /Y /E /Q include %INCLIB%
+copy /Y /B "objs\Win32\Release Static\freetype.lib" %INCLIB%
+endlocal
+
+rem -> Build LCMS2
+setlocal
+cd /D %BUILD%\lcms2-2.8
+rmdir /S /Q Lib
+rmdir /S /Q Projects\VC2015\Release
+set VCTargetsPath=C:\BuildTools\MSBuild\Microsoft\VC\v160\
+set MSBUILD="C:\BuildTools\MSBuild\Current\Bin\MSBuild.exe"
+powershell C:\Pillow\winbuild\lcms2_patch.ps1
+%MSBUILD% Projects\VC2015\lcms2.sln /t:Clean;lcms2_static /p:Configuration="Release" /p:Platform=Win32 /m
+xcopy /Y /E /Q include %INCLIB%
+copy /Y /B Lib\MS\*.lib %INCLIB%
+endlocal
+
+rem -> Build OpenJPEG
+setlocal
+cd /D %BUILD%\openjpeg-2.3.1msvcr10-x32
+set CMAKE=cmake.exe -DCMAKE_VERBOSE_MAKEFILE=ON -DCMAKE_RULE_MESSAGES:BOOL=OFF
+set CMAKE=%CMAKE% -DBUILD_THIRDPARTY:BOOL=OFF -DBUILD_SHARED_LIBS:BOOL=OFF
+set CMAKE=%CMAKE% -DCMAKE_BUILD_TYPE=Release
+%CMAKE% -G "NMake Makefiles" .
+nmake -nologo -f Makefile clean
+nmake -nologo -f Makefile
+mkdir %INCLIB%\openjpeg-2.3.1
+copy /Y /B src\lib\openjp2\*.h %INCLIB%\openjpeg-2.3.1
+copy /Y /B bin\*.lib %INCLIB%
+endlocal
+
+rem -> Build libimagequant
+setlocal
+rem e5d454b: Merge tag '2.12.6' into msvc
+cd /D %BUILD%\libimagequant-e5d454bc7f5eb63ee50c84a83a7fa5ac94f68ec4
+echo (gc CMakeLists.txt) -replace 'add_library', "add_compile_options(-openmp-)`r`nadd_library" ^| Out-File -encoding ASCII CMakeLists.txt > patch.ps1
+echo (gc CMakeLists.txt) -replace ' SHARED', ' STATIC' ^| Out-File -encoding ASCII CMakeLists.txt >> patch.ps1
+powershell .\patch.ps1
+set CMAKE=cmake.exe -DCMAKE_VERBOSE_MAKEFILE=ON -DCMAKE_RULE_MESSAGES:BOOL=OFF
+set CMAKE=%CMAKE% -DCMAKE_BUILD_TYPE=Release
+%CMAKE% -G "NMake Makefiles" .
+nmake -nologo -f Makefile clean
+nmake -nologo -f Makefile
+copy /Y /B *.h %INCLIB%
+copy /Y /B *.lib %INCLIB%
+endlocal
+
+rem -> Build HarfBuzz
+setlocal
+set INCLUDE=%INCLUDE%;%INCLIB%
+set LIB=%LIB%;%INCLIB%
+cd /D %BUILD%\harfbuzz-2.6.1
+set CMAKE=cmake.exe -DCMAKE_VERBOSE_MAKEFILE=ON -DCMAKE_RULE_MESSAGES:BOOL=OFF
+set CMAKE=%CMAKE% -DHB_HAVE_FREETYPE:BOOL=ON -DCMAKE_BUILD_TYPE=Release
+%CMAKE% -G "NMake Makefiles" .
+nmake -nologo -f Makefile clean
+nmake -nologo -f Makefile harfbuzz
+copy /Y /B src\*.h %INCLIB%
+copy /Y /B *.lib %INCLIB%
+endlocal
+
+rem -> Build FriBidi
+setlocal
+cd /D %BUILD%\fribidi-1.0.7
+copy /Y /B C:\Pillow\winbuild\fribidi.cmake CMakeLists.txt
+set CMAKE=cmake.exe -DCMAKE_VERBOSE_MAKEFILE=ON -DCMAKE_RULE_MESSAGES:BOOL=OFF
+set CMAKE=%CMAKE% -DCMAKE_BUILD_TYPE=Release
+%CMAKE% -G "NMake Makefiles" .
+nmake -nologo -f Makefile clean
+nmake -nologo -f Makefile fribidi
+copy /Y /B lib\*.h %INCLIB%
+copy /Y /B *.lib %INCLIB%
+endlocal
+
+rem -> Build Raqm
+setlocal
+set INCLUDE=%INCLUDE%;%INCLIB%
+set LIB=%LIB%;%INCLIB%
+cd /D %BUILD%\libraqm-0.7.0
+copy /Y /B C:\Pillow\winbuild\raqm.cmake CMakeLists.txt
+set CMAKE=cmake.exe -DCMAKE_VERBOSE_MAKEFILE=ON -DCMAKE_RULE_MESSAGES:BOOL=OFF
+set CMAKE=%CMAKE% -DCMAKE_BUILD_TYPE=Release
+%CMAKE% -G "NMake Makefiles" .
+nmake -nologo -f Makefile clean
+nmake -nologo -f Makefile libraqm
+copy /Y /B src\*.h %INCLIB%
+copy /Y /B libraqm.dll %INCLIB%
+endlocal
+
+rem Build Pillow
+cd c:\pillow\
+set PYTHON=C:\Python37\
+set MPLSRC=C:\Pillow\
+set LIB=%INCLIB%;%PYTHON%\tcl;%LIB%
+set INCLUDE=%INCLIB%;C:\Pillow\depends\tcl86\include;%INCLUDE%
+set MSSdk=1
+set DISTUTILS_USE_SDK=1
+set py_vcruntime_redist=true
+c:\python37\python.exe setup.py build_ext install
+
+rem Test Pillow
+cd c:\pillow
+path %INCLIB%;%PATH%
+c:\python37\python.exe selftest.py --installed
+c:\python37\python.exe -m pytest -vx -W always --cov PIL --cov Tests --cov-report term --cov-report xml Tests