diff --git a/.gitlab-ci.yml b/.gitlab-ci.yml
index 60a5bc0e7f..356afb5264 100644
--- a/.gitlab-ci.yml
+++ b/.gitlab-ci.yml
@@ -25,7 +25,7 @@ variables:
   ###
   FEDORA_TAG:  '2021-10-05.0'
   INDENT_TAG: '2021-10-04.0'
-  WINDOWS_TAG: "2021-10-04.1"
+  WINDOWS_TAG: "2021-10-12.0"
 
   GST_UPSTREAM_REPO: 'gstreamer/gstreamer'
   FDO_UPSTREAM_REPO: 'gstreamer/gstreamer'
diff --git a/ci/docker/windows/Dockerfile b/ci/docker/windows/Dockerfile
index 9637c2e7bb..260b467865 100644
--- a/ci/docker/windows/Dockerfile
+++ b/ci/docker/windows/Dockerfile
@@ -6,13 +6,41 @@ FROM 'mcr.microsoft.com/windows/servercore:ltsc2019'
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop';"]
 ENV ErrorActionPreference='Stop'
 
-COPY install_choco.ps1 C:\
-RUN C:\install_choco.ps1
+# Install Chocolatey
+RUN iex ((New-Object System.Net.WebClient).DownloadString('https://chocolatey.org/install.ps1'))
+# Install required packages
+RUN choco install -y vcredist140
+RUN choco install -y cmake --installargs 'ADD_CMAKE_TO_PATH=System'
+RUN choco install -y git --params '/NoAutoCrlf /NoCredentialManager /NoShellHereIntegration /NoGuiHereIntegration /NoShellIntegration'
+RUN choco install -y git-lfs
+RUN choco install -y 7zip
+RUN choco install -y windows-sdk-8.1
+RUN choco install -y python3
+RUN choco install -y msys2 --params '/NoPath /NoUpdate /InstallDir:C:\\msys64'
+
+# Visual Studio can't be installed with choco.
+# It depends on dotnetfx v4.8.0.20190930, which requires a reboot: dotnetfx (exit code 3010)
+# https://github.com/microsoft/vs-dockerfiles/blob/main/native-desktop/
+# Set up environment to collect install errors.
+COPY Install.cmd C:\TEMP\
+ADD https://aka.ms/vscollect.exe C:\TEMP\collect.exe
+# Download channel for fixed install.
+ARG CHANNEL_URL=https://aka.ms/vs/15/release/channel
+ADD ${CHANNEL_URL} C:\TEMP\VisualStudio.chman
+# Download and install Build Tools for Visual Studio 2017 for native desktop workload.
+ADD https://aka.ms/vs/15/release/vs_buildtools.exe C:\TEMP\vs_buildtools.exe
+RUN C:\TEMP\Install.cmd C:\TEMP\vs_buildtools.exe --quiet --wait --norestart --nocache `
+    --channelUri C:\TEMP\VisualStudio.chman `
+    --installChannelUri C:\TEMP\VisualStudio.chman `
+    --add Microsoft.VisualStudio.Workload.VCTools --includeRecommended`
+    --installPath C:\BuildTools
+
+RUN pip3 install meson
 
 RUN 'git config --global user.email "cirunner@gstreamer.freedesktop.org"; git config --global user.name "GStreamer CI system"'
 
-COPY install_toolchain.ps1 C:\
-RUN C:\install_toolchain.ps1
+COPY install_mingw.ps1 C:\
+RUN C:\install_mingw.ps1
 
 ARG DEFAULT_BRANCH="main"
 
@@ -20,4 +48,4 @@ COPY prepare_gst_env.ps1 C:\
 RUN C:\prepare_gst_env.ps1
 
 COPY prepare_cerbero_env.sh  C:\
-RUN C:\MinGW\msys\1.0\bin\bash.exe --login -c "C:/prepare_cerbero_env.sh"
+RUN C:\MinGW\msys\1.0\bin\bash.exe --login -c "C:/prepare_cerbero_env.sh"
\ No newline at end of file
diff --git a/ci/docker/windows/Install.cmd b/ci/docker/windows/Install.cmd
new file mode 100644
index 0000000000..a0c07c7815
--- /dev/null
+++ b/ci/docker/windows/Install.cmd
@@ -0,0 +1,17 @@
+@rem Copyright (C) Microsoft Corporation. All rights reserved.
+@rem Licensed under the MIT license. See LICENSE.txt in the project root for license information.
+
+@if not defined _echo echo off
+setlocal enabledelayedexpansion
+
+call %*
+if "%ERRORLEVEL%"=="3010" (
+    exit /b 0
+) else (
+    if not "%ERRORLEVEL%"=="0" (
+        set ERR=%ERRORLEVEL%
+        call C:\TEMP\collect.exe -zip:C:\vslogs.zip
+
+        exit /b !ERR!
+    )
+)
diff --git a/ci/docker/windows/install_choco.ps1 b/ci/docker/windows/install_choco.ps1
deleted file mode 100644
index 8fc6897086..0000000000
--- a/ci/docker/windows/install_choco.ps1
+++ /dev/null
@@ -1,26 +0,0 @@
-Get-Date
-Write-Host "Installing Chocolatey"
-Set-ExecutionPolicy Bypass -Scope Process -Force;
-# Force TLS 1.2
-[System.Net.ServicePointManager]::SecurityProtocol = [System.Net.ServicePointManager]::SecurityProtocol -bor 3072;
-iex ((New-Object System.Net.WebClient).DownloadString('https://community.chocolatey.org/install.ps1'))
-Import-Module "$env:ProgramData\chocolatey\helpers\chocolateyProfile.psm1"
-Update-SessionEnvironment
-
-choco install -y vcredist140
-$vc140_install = $?
-
-Write-Host "Installing Chocolatey packages"
-choco install -y cmake --installargs 'ADD_CMAKE_TO_PATH=System'
-$cmake_install = $?
-
-choco install -y git --params "/NoAutoCrlf /NoCredentialManager /NoShellHereIntegration /NoGuiHereIntegration /NoShellIntegration"
-$git_install = $?
-
-choco install -y python3 git-lfs 7zip
-$rest_installs = $?
-
-if (!($vc140_install -and $cmake_install -and $git_install -and $rest_installs)) {
-    Write-Host "Failed to install some dependencies from choco"
-    Exit 1
-}
diff --git a/ci/docker/windows/install_mingw.ps1 b/ci/docker/windows/install_mingw.ps1
new file mode 100644
index 0000000000..e7542369b2
--- /dev/null
+++ b/ci/docker/windows/install_mingw.ps1
@@ -0,0 +1,29 @@
+[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12;
+
+$msys_mingw_get_url = 'https://dotsrc.dl.osdn.net/osdn/mingw/68260/mingw-get-0.6.3-mingw32-pre-20170905-1-bin.tar.xz'
+
+Get-Date
+Write-Host "Downloading and extracting mingw-get for MSYS"
+Invoke-WebRequest -Uri $msys_mingw_get_url -OutFile C:\mingw-get.tar.xz
+7z e C:\mingw-get.tar.xz -o"C:\\"
+$res1 = $?
+7z x C:\mingw-get.tar -o"C:\\MinGW"
+$res2 = $?
+
+if (!($res1 -and $res2)) {
+  Write-Host "Failed to extract mingw-get"
+  Exit 1
+}
+
+Remove-Item C:\mingw-get.tar.xz -Force
+Remove-Item C:\mingw-get.tar -Force
+
+Get-Date
+Write-Host "Installing MSYS for Cerbero into C:/MinGW using mingw-get"
+Start-Process -Wait C:\MinGW\bin\mingw-get.exe -ArgumentList 'install msys-base mingw32-base mingw-developer-toolkit'
+if (!$?) {
+  Write-Host "Failed to install Msys for cerbero using MinGW"
+  Exit 1
+}
+
+Write-Host "MSYS/MinGW Install Complete"
diff --git a/ci/docker/windows/install_toolchain.ps1 b/ci/docker/windows/install_toolchain.ps1
deleted file mode 100644
index fd61b42d1c..0000000000
--- a/ci/docker/windows/install_toolchain.ps1
+++ /dev/null
@@ -1,69 +0,0 @@
-[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12;
-
-$msvc_2017_url = 'https://aka.ms/vs/15/release/vs_buildtools.exe'
-$msys2_url = 'https://github.com/msys2/msys2-installer/releases/download/2021-02-15/msys2-base-x86_64-20210215.tar.xz'
-$msys_mingw_get_url = 'https://dotsrc.dl.osdn.net/osdn/mingw/68260/mingw-get-0.6.3-mingw32-pre-20170905-1-bin.tar.xz'
-
-Get-Date
-Write-Host "Downloading Visual Studio 2017 build tools"
-Invoke-WebRequest -Uri $msvc_2017_url -OutFile C:\vs_buildtools.exe
-
-Get-Date
-Write-Host "Installing Visual Studio 2017"
-Start-Process -NoNewWindow -Wait C:\vs_buildtools.exe -ArgumentList '--wait --quiet --norestart --nocache --installPath C:\BuildTools --add Microsoft.VisualStudio.Workload.VCTools --includeRecommended'
-if (!$?) {
-  Write-Host "Failed to install Visual Studio tools"
-  Exit 1
-}
-Remove-Item C:\vs_buildtools.exe -Force
-
-Get-Date
-Write-Host "Downloading and extracting mingw-get for MSYS"
-Invoke-WebRequest -Uri $msys_mingw_get_url -OutFile C:\mingw-get.tar.xz
-7z e C:\mingw-get.tar.xz -o"C:\\"
-$res1 = $?
-7z x C:\mingw-get.tar -o"C:\\MinGW"
-$res2 = $?
-
-if (!($res1 -and $res2)) {
-  Write-Host "Failed to extract mingw-get"
-  Exit 1
-}
-
-Remove-Item C:\mingw-get.tar.xz -Force
-Remove-Item C:\mingw-get.tar -Force
-
-Get-Date
-Write-Host "Installing MSYS for Cerbero into C:/MinGW using mingw-get"
-Start-Process -Wait C:\MinGW\bin\mingw-get.exe -ArgumentList 'install msys-base mingw32-base mingw-developer-toolkit'
-if (!$?) {
-  Write-Host "Failed to install Msys for cerbero using MinGW"
-  Exit 1
-}
-
-Get-Date
-Write-Host "Installing MSYS2 into C:/msys64"
-Invoke-WebRequest -Uri $msys2_url -OutFile C:\msys2-x86_64.tar.xz
-
-7z e C:\msys2-x86_64.tar.xz -o"C:\\"
-$res1 = $?
-7z x C:\msys2-x86_64.tar -o"C:\\"
-$res2 = $?
-
-if (!($res1 -and $res2)) {
-  Write-Host "Failed to extract msys2"
-  Exit 1
-}
-
-Remove-Item C:\msys2-x86_64.tar.xz -Force
-Remove-Item C:\msys2-x86_64.tar -Force
-
-Get-Date
-Write-Host "Installing Meson"
-pip3 install meson
-if (!$?) {
-  Write-Host "Failed to install meson from pip"
-  Exit 1
-}
-
-Write-Host "Toolchain Install Complete"