diff --git a/docker/windows/Dockerfile b/docker/windows/Dockerfile
index e0b8244141..e8430606a9 100644
--- a/docker/windows/Dockerfile
+++ b/docker/windows/Dockerfile
@@ -1,6 +1,6 @@
 # escape=`
 
-FROM 'mcr.microsoft.com/windows/servercore:1607'
+FROM 'mcr.microsoft.com/windows/servercore:1809'
 
 # Make sure any failure in PowerShell scripts is fatal
 SHELL ["powershell", "-Command", "$ErrorActionPreference = 'Stop';"]
@@ -9,4 +9,4 @@ COPY install_toolchain.ps1 prepare_gst_env.ps1 C:\
 
 RUN C:\install_toolchain.ps1
 
-RUN C:\prepare_gst_env.ps1
\ No newline at end of file
+RUN C:\prepare_gst_env.ps1
diff --git a/docker/windows/install_toolchain.ps1 b/docker/windows/install_toolchain.ps1
index 6c224e05d6..2d4260ec0c 100644
--- a/docker/windows/install_toolchain.ps1
+++ b/docker/windows/install_toolchain.ps1
@@ -44,9 +44,7 @@ Write-Host "Installing git-lfs"
 choco install -y git-lfs
 refreshenv
 
-$env:PATH += ";C:\msys64\usr\bin;C:\msys64\mingw64/bin;C:\msys64\mingw32/bin"
-C:\msys64\usr\bin\bash -c "pacman-key --init && pacman-key --populate msys2 && pacman-key --refresh-keys"
-C:\msys64\usr\bin\bash -c "pacman -Syuu --noconfirm"
-C:\msys64\usr\bin\bash -c "pacman -Sy --noconfirm --needed mingw-w64-x86_64-toolchain ninja"
-
+Write-Host "Installing Meson"
 pip install meson
+
+Write-Host "Complete"
diff --git a/gitlab/ci_template.yml b/gitlab/ci_template.yml
index e516024a23..7466700422 100644
--- a/gitlab/ci_template.yml
+++ b/gitlab/ci_template.yml
@@ -12,7 +12,7 @@ variables:
   FEDORA_IMAGE: 'registry.freedesktop.org/gstreamer/gst-ci/amd64/fedora:2019-10-23-793478'
   INDENT_IMAGE: 'registry.freedesktop.org/gstreamer/gst-ci/amd64/gst-indent:6f7e01e1e30a73efa880acdc8e911f1f20c58dbb'
   MANIFEST_IMAGE: 'registry.freedesktop.org/gstreamer/gst-ci/amd64/build-manifest:2019-10-23-793475'
-  WINDOWS_IMAGE: 'registry.freedesktop.org/gstreamer/gst-ci/amd64/windows:v7'
+  WINDOWS_IMAGE: 'registry.freedesktop.org/gstreamer/gst-ci/amd64/windows:v8'
 
   # Branch to track for modules that have no ref specified in the manifest
   GST_UPSTREAM_BRANCH: 'master'
@@ -411,8 +411,8 @@ valgrind ges:
   tags:
     - 'docker'
     - 'windows'
-    - '1607'
-  timeout: '15min'
+    - '1809'
+  timeout: '45min'
   variables:
     MESON_ARGS: >
       ${DEFAULT_MESON_ARGS}
@@ -424,6 +424,8 @@ valgrind ges:
     - git clone https://gitlab.freedesktop.org/gstreamer/gst-build.git $env:CI_PROJECT_DIR/gst-build
     - cd $env:CI_PROJECT_DIR/gst-build
     - cp -r C:/subprojects/* subprojects/
+    # Run the git-update script and feed it the manifest to setup the environment
+    - cd $env:CI_PROJECT_DIR/gst-build && python git-update --no-interaction --manifest=$env:CI_PROJECT_DIR/manifest.xml
     # For some reason, options are separated by newline instead of space, so we
     # have to replace them first.
     - $env:MESON_ARGS = $env:MESON_ARGS.replace("`n"," ")
@@ -431,7 +433,6 @@ valgrind ges:
     # Environment variables substitutions is done by PowerShell before calling
     # cmd.exe, that's why we use $env:FOO instead of %FOO%
     - cmd.exe /C "C:\BuildTools\Common7\Tools\VsDevCmd.bat -host_arch=amd64 -arch=$env:ARCH &&
-        python git-update --no-interaction --manifest=$env:CI_PROJECT_DIR/manifest.xml &&
         meson build $env:MESON_ARGS &&
         ninja -C build"
   # FIXME: extract builddir for tests
@@ -463,16 +464,24 @@ build vs2017 x86:
 build msys2 :
   extends: '.build windows'
   script:
-    - git clone https://gitlab.freedesktop.org/gstreamer/gst-build.git $env:CI_PROJECT_DIR/gst-build
-    - cd $env:CI_PROJECT_DIR/gst-build
-    - cp -r C:/subprojects/* subprojects/
+    # For some reason docker build hangs if this is included in the image, needs more troubleshooting
+    - $env:PATH += ';C:\msys64\usr\bin;C:\msys64\mingw64\bin;C:\msys64\mingw32\bin'
+    - C:\msys64\usr\bin\bash -c "pacman-key --init && pacman-key --populate msys2 && pacman-key --refresh-keys || true"
+    - C:\msys64\usr\bin\bash -c "pacman -Syuu --noconfirm"
+    - C:\msys64\usr\bin\bash -c "pacman -Sy --noconfirm --needed mingw-w64-x86_64-toolchain ninja"
 
-    - $env:PATH += ";C:\msys64\usr\bin;C:\msys64\mingw64/bin;C:\msys64\mingw32/bin"
+    - git clone https://gitlab.freedesktop.org/gstreamer/gst-build.git $env:CI_PROJECT_DIR\gst-build
+    - cd $env:CI_PROJECT_DIR\gst-build
+    - cp -r C:\subprojects\* subprojects\
+
+    # Run the git-update script and feed it the manifest to setup the environment
+    - cd $env:CI_PROJECT_DIR/gst-build && python git-update --no-interaction --manifest=$env:CI_PROJECT_DIR/manifest.xml
     # For some reason, options are separated by newline instead of space, so we
     # have to replace them first.
     - $env:MESON_ARGS = $env:MESON_ARGS.replace("`n"," ")
-    - C:\msys64\usr\bin\bash -c "cd $env:CI_PROJECT_DIR/gst-build &&
-        python git-update --no-interaction --manifest=$env:CI_PROJECT_DIR/manifest.xml &&
+    # Replace forward slashes with backwards so bash doesn't complain
+    - $env:_PROJECT_DIR = $env:CI_PROJECT_DIR.replace('\','/')
+    - C:\msys64\usr\bin\bash -c "cd $env:_PROJECT_DIR/gst-build &&
         meson build $env:MESON_ARGS &&
         ninja -C build"