diff --git a/.gitlab-ci.yml b/.gitlab-ci.yml
index 30f6d7f2b5..923debee74 100644
--- a/.gitlab-ci.yml
+++ b/.gitlab-ci.yml
@@ -26,7 +26,7 @@ variables:
   ###
   FEDORA_TAG:  '2022-07-31.0'
   INDENT_TAG: '2022-03-07.1'
-  WINDOWS_TAG: "2022-07-31.0"
+  WINDOWS_TAG: "2022-08-18.0"
 
   GST_UPSTREAM_REPO: 'gstreamer/gstreamer'
   FDO_UPSTREAM_REPO: 'gstreamer/gstreamer'
diff --git a/ci/docker/windows/Dockerfile b/ci/docker/windows/Dockerfile
index d6628b7afd..eefa8b55c5 100644
--- a/ci/docker/windows/Dockerfile
+++ b/ci/docker/windows/Dockerfile
@@ -16,7 +16,7 @@ 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 python3
+RUN choco install -y python3 --installargs 'AssociateFiles=1 PrependPath=1 Include_pip=1 Include_dev=1'
 RUN choco install -y msys2 --params '/NoPath /NoUpdate /InstallDir:C:\\msys64'
 
 # Remove MAX_PATH limit of 260 characters