diff --git a/ci/docker/windows/Dockerfile b/ci/docker/windows/Dockerfile
index 17418c97c2..3aa80dfb44 100644
--- a/ci/docker/windows/Dockerfile
+++ b/ci/docker/windows/Dockerfile
@@ -49,15 +49,15 @@ RUN New-ItemProperty -Path 'HKLM:\\SYSTEM\\CurrentControlSet\\Control\\FileSyste
     -Name "LongPathsEnabled" -Value 1 -PropertyType DWORD -Force
 RUN git config --system core.longpaths true
 
-RUN c:\msys64\usr\bin\bash -lc 'pacman -S --noconfirm mingw-w64-ucrt-x86_64-toolchain ninja'
+COPY upgrade_msys2.ps1 C:\
+RUN C:\upgrade_msys2.ps1
 
-RUN pip3 install meson==1.1.1
+RUN C:\msys64\msys2_shell.cmd -ucrt64 -defterm -here -no-start -use-full-path -lc 'pacman -S --noconfirm mingw-w64-ucrt-x86_64-toolchain ninja'
+
+RUN python -m pip install meson==1.1.1
 
 RUN 'git config --global user.email "cirunner@gstreamer.freedesktop.org"; git config --global user.name "GStreamer CI system"'
 
-COPY install_mingw.ps1 C:\
-RUN C:\install_mingw.ps1
-
 COPY install_rust.ps1 C:\
 RUN C:\install_rust.ps1
 
@@ -67,4 +67,4 @@ 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:\msys64\msys2_shell.cmd -ucrt64 -defterm -here -no-start -use-full-path -lc "C:/prepare_cerbero_env.sh"
diff --git a/ci/docker/windows/install_mingw.ps1 b/ci/docker/windows/install_mingw.ps1
deleted file mode 100644
index e7542369b2..0000000000
--- a/ci/docker/windows/install_mingw.ps1
+++ /dev/null
@@ -1,29 +0,0 @@
-[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/prepare_cerbero_env.sh b/ci/docker/windows/prepare_cerbero_env.sh
index 90fb80c765..eb1dd07454 100644
--- a/ci/docker/windows/prepare_cerbero_env.sh
+++ b/ci/docker/windows/prepare_cerbero_env.sh
@@ -18,7 +18,7 @@ echo 'vs_install_version = "vs17"' >> localconf.cbc
 # Fetch all package requirements for a visualstudio gstreamer build
 ./cerbero-uninstalled -t -v visualstudio -c localconf.cbc -c config/win64.cbc fetch-package --jobs=4 gstreamer-1.0
 
-# Fixup the MSYS installation
+# Fixup the MSYS2 installation
 ./cerbero-uninstalled -t -c localconf.cbc -c config/win64.cbc bootstrap -y --build-tools=no --toolchains=no --offline
 
 # Wipe visualstudio package dist, sources, logs, and the build tools recipes
diff --git a/ci/docker/windows/upgrade_msys2.ps1 b/ci/docker/windows/upgrade_msys2.ps1
new file mode 100644
index 0000000000..de1638b23e
--- /dev/null
+++ b/ci/docker/windows/upgrade_msys2.ps1
@@ -0,0 +1,11 @@
+$ErrorActionPreference = 'Continue'
+# Perform a sysupgrade on MSYS2, otherwise it will do the upgrade at a later stage
+while (1) {
+  C:\msys64\msys2_shell.cmd -ucrt64 -defterm -here -no-start -use-full-path -lc 'pacman -Syuu --noconfirm'
+  if (!$?) {
+    Write-Host "System upgrade needed to kill MSYS2 processes or something, running it again..."
+    continue
+  }
+  Write-Host "MSYS2 system upgrade complete"
+  break
+}