diff --git a/.github/workflows/windows-docker-image.yaml b/.github/workflows/windows-docker-image.yaml
index 40655ff7b..8d2b7d0cc 100644
--- a/.github/workflows/windows-docker-image.yaml
+++ b/.github/workflows/windows-docker-image.yaml
@@ -22,9 +22,9 @@ on:
   push:
     # Will only trigger building a docker image if any of these changed
     paths:
-    - '.github/docker/rez-win-base/**'
-    - '.github/docker/rez-win-py/**'
-    - '.github/workflows/windows-docker-image.yaml'
+      - '.github/docker/rez-win-base/**'
+      - '.github/docker/rez-win-py/**'
+      - '.github/workflows/windows-docker-image.yaml'
 
 jobs:
 
@@ -51,13 +51,14 @@ jobs:
         run: |
           ${Env:LAST_DOCKER_BASE_REVISION} = $( git log -n 1 --author-date-order --pretty=format:%H -- .\.github\docker\rez-win-base\  .\.github\workflows\windows-docker-image.yaml ).SubString(0, 8)
           ${gh_user} = ("${{ github.repository }}" -Split '/')[0]
+          $ErrorActionPreference = "Continue"
           docker manifest inspect ${gh_user}/rez-win-base:${ENV:LAST_DOCKER_BASE_REVISION} | Out-Null
-          if (-not $?) {
+          $ErrorActionPreference = "Stop"
+          if ($LastExitCode -ne 0) {
             cd .github\docker\rez-win-base
             docker build --tag ${gh_user}/rez-win-base:${ENV:LAST_DOCKER_BASE_REVISION} .
             docker push ${gh_user}/rez-win-base:${ENV:LAST_DOCKER_BASE_REVISION}
           }
-
         env:
           DOCKER_CLI_EXPERIMENTAL: enabled
 
@@ -92,12 +93,20 @@ jobs:
           docker pull ${gh_user}/rez-win-base:${ENV:LAST_DOCKER_BASE_REVISION}
           docker tag ${gh_user}/rez-win-base:${ENV:LAST_DOCKER_BASE_REVISION} rez-win-base:${ENV:LAST_DOCKER_BASE_REVISION}
 
-      - name: Build and push Docker image
+      - name: Build Docker image if needed
         run: |
-          ${gh_user} = ("${{ github.repository }}" -Split '/')[0]
-          ${ENV:DOCKER_TAG} = "${{ github.sha }}".Substring(0, 8)
           ${Env:LAST_DOCKER_BASE_REVISION} = $( git log -n 1 --author-date-order --pretty=format:%H -- .\.github\docker\rez-win-base\  .\.github\workflows\windows-docker-image.yaml ).SubString(0, 8)
-          cd .github\docker\rez-win-py
-          docker build --tag ${gh_user}/rez-win-py:${{ matrix.python-version }}-${ENV:DOCKER_TAG} --build-arg PYTHON_VERSION="${{ matrix.python-version }}" --build-arg BASE_TAG=${ENV:LAST_DOCKER_BASE_REVISION} .
-          docker push ${gh_user}/rez-win-py:${{ matrix.python-version }}-${ENV:DOCKER_TAG}
-
+          ${Env:LAST_DOCKER_PY_REVISION} = $( git log -n 1 --author-date-order --pretty=format:%H -- .\.github\docker\rez-win-py\ .\.github\docker\rez-win-base\ .\.github\workflows\windows-docker-image.yaml ).SubString(0, 8)
+          ${Env:DOCKER_TAG} = "${{ matrix.python-version }}-${ENV:LAST_DOCKER_PY_REVISION}"
+          ${gh_user} = ("${{ github.repository }}" -Split '/')[0]
+          $ErrorActionPreference = "Continue"
+          docker manifest inspect ${gh_user}/rez-win-py:${ENV:DOCKER_TAG} | Out-Null
+          $ErrorActionPreference = "Stop"
+          if ($LastExitCode -ne 0) {
+            cd .github\docker\rez-win-py
+            docker build --tag ${gh_user}/rez-win-py:${ENV:DOCKER_TAG} --build-arg PYTHON_VERSION="${{ matrix.python-version }}" --build-arg BASE_TAG=${ENV:LAST_DOCKER_BASE_REVISION} .
+            docker push ${gh_user}/rez-win-py:${ENV:DOCKER_TAG}
+          }
+          $ErrorActionPreference = "Stop"
+        env:
+          DOCKER_CLI_EXPERIMENTAL: enabled
diff --git a/.github/workflows/windows.yaml b/.github/workflows/windows.yaml
index 35309ed3c..978a566b3 100644
--- a/.github/workflows/windows.yaml
+++ b/.github/workflows/windows.yaml
@@ -47,12 +47,12 @@ jobs:
       - name: Pull docker image
         run: |
           ${gh_user} = ("${{ github.repository }}" -Split '/')[0]
-          ${Env:LAST_DOCKER_REVISION} = $( git log -n 1 --author-date-order --pretty=format:%H -- .\.github\docker\rez-win-py\  .\.github\workflows\windows-docker-image.yaml ).SubString(0, 8)
+          ${Env:LAST_DOCKER_REVISION} = $( git log -n 1 --author-date-order --pretty=format:%H -- .\.github\docker\rez-win-py\ .\.github\docker\rez-win-base\ .\.github\workflows\windows-docker-image.yaml ).SubString(0, 8)
           echo "Pulling rez-win-py:${{ matrix.python-version }}-${Env:LAST_DOCKER_REVISION}"
           docker pull ${gh_user}/rez-win-py:${{ matrix.python-version }}-${Env:LAST_DOCKER_REVISION}
 
       - name: Run Docker image (installs and tests rez)
         run: |
           ${gh_user} = ("${{ github.repository }}" -Split '/')[0]
-          ${Env:LAST_DOCKER_REVISION} = $( git log -n 1 --author-date-order --pretty=format:%H -- .\.github\docker\rez-win-py\  .\.github\workflows\windows-docker-image.yaml ).SubString(0, 8)
+          ${Env:LAST_DOCKER_REVISION} = $( git log -n 1 --author-date-order --pretty=format:%H -- .\.github\docker\rez-win-py\ .\.github\docker\rez-win-base\ .\.github\workflows\windows-docker-image.yaml ).SubString(0, 8)
           docker run ${gh_user}/rez-win-py:${{ matrix.python-version }}-${Env:LAST_DOCKER_REVISION} ${{ github.repository }} ${{ github.sha }}