diff --git a/.github/scripts/push_with_image_map.py b/.github/scripts/push_with_image_map.py
index c68f6ad407..53f83379ae 100644
--- a/.github/scripts/push_with_image_map.py
+++ b/.github/scripts/push_with_image_map.py
@@ -11,12 +11,27 @@ try:
 except json.JSONDecodeError as e:
     raise ValueError("Failed to parse IMAGE_MAP as JSON") from e
 
-for source, targets in parsed_image_map.items():
-    for target in targets:
-        cmd = ["docker", "buildx", "imagetools", "create", "-t", target, source]
-        print(f"Running: {' '.join(cmd)}")
-        result = subprocess.run(cmd, text=True, stdout=subprocess.PIPE, stderr=subprocess.STDOUT)
+failures = []
 
-        if result.returncode != 0:
-            print(f"Error: {result.stdout}")
-            raise RuntimeError(f"Command failed: {' '.join(cmd)}")
+pending = [(source, target) for source, targets in parsed_image_map.items() for target in targets]
+
+while len(pending) > 0:
+    if len(failures) > 10:
+        print("Error: more than 10 failures!")
+        for failure in failures:
+            print(f'"{failure[0]}" failed with the following output:')
+            print(failure[1])
+        raise RuntimeError("Retry limit reached.")
+
+    source, target = pending.pop(0)
+    cmd = ["docker", "buildx", "imagetools", "create", "-t", target, source]
+    print(f"Running: {' '.join(cmd)}")
+    result = subprocess.run(cmd, text=True, stdout=subprocess.PIPE, stderr=subprocess.STDOUT)
+
+    if result.returncode != 0:
+        failures.append((" ".join(cmd), result.stdout))
+        pending.append((source, target))
+
+if len(failures) > 0 and (github_output := os.getenv("GITHUB_OUTPUT")):
+    with open(github_output, "a") as f:
+        f.write("slack_notify=true\n")
diff --git a/.github/workflows/_push-to-container-registry.yml b/.github/workflows/_push-to-container-registry.yml
index 9a7da612d4..9b3ad0fdbb 100644
--- a/.github/workflows/_push-to-container-registry.yml
+++ b/.github/workflows/_push-to-container-registry.yml
@@ -104,6 +104,18 @@ jobs:
           password: ${{ secrets.NEON_DOCKERHUB_PASSWORD }}
 
       - name: Copy docker images to target registries
+        id: push
         run: python3 .github/scripts/push_with_image_map.py
         env:
           IMAGE_MAP: ${{ inputs.image-map }}
+
+      - name: Notify Slack if container image pushing fails
+        if: steps.push.outputs.slack_notify == 'true' || failure()
+        uses: slackapi/slack-github-action@485a9d42d3a73031f12ec201c457e2162c45d02d # v2.0.0
+        with:
+          method: chat.postMessage
+          token: ${{ secrets.SLACK_BOT_TOKEN }}
+          payload: |
+            channel: ${{ vars.SLACK_ON_CALL_DEVPROD_STREAM }}
+            text: |
+              Pushing container images failed in <${{ github.server_url }}/${{ github.repository }}/actions/runs/${{ github.run_id }}|GitHub Run>