diff --git a/.github/scripts/push_with_image_map.py b/.github/scripts/push_with_image_map.py
index 53f83379ae..85e2eb1937 100644
--- a/.github/scripts/push_with_image_map.py
+++ b/.github/scripts/push_with_image_map.py
@@ -2,6 +2,9 @@ import json
 import os
 import subprocess
 
+RED = "\033[91m"
+RESET = "\033[0m"
+
 image_map = os.getenv("IMAGE_MAP")
 if not image_map:
     raise ValueError("IMAGE_MAP environment variable is not set")
@@ -29,9 +32,14 @@ while len(pending) > 0:
     result = subprocess.run(cmd, text=True, stdout=subprocess.PIPE, stderr=subprocess.STDOUT)
 
     if result.returncode != 0:
-        failures.append((" ".join(cmd), result.stdout))
+        failures.append((" ".join(cmd), result.stdout, target))
         pending.append((source, target))
+        print(
+            f"{RED}[RETRY]{RESET} Push failed for {target}. Retrying... (failure count: {len(failures)})"
+        )
+        print(result.stdout)
 
 if len(failures) > 0 and (github_output := os.getenv("GITHUB_OUTPUT")):
+    failed_targets = [target for _, _, target in failures]
     with open(github_output, "a") as f:
-        f.write("slack_notify=true\n")
+        f.write(f"push_failures={json.dumps(failed_targets)}\n")
diff --git a/.github/workflows/_push-to-container-registry.yml b/.github/workflows/_push-to-container-registry.yml
index 9b3ad0fdbb..7d3a11409b 100644
--- a/.github/workflows/_push-to-container-registry.yml
+++ b/.github/workflows/_push-to-container-registry.yml
@@ -110,12 +110,19 @@ jobs:
           IMAGE_MAP: ${{ inputs.image-map }}
 
       - name: Notify Slack if container image pushing fails
-        if: steps.push.outputs.slack_notify == 'true' || failure()
+        if: steps.push.outputs.push_failures || 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>
+            text: >
+              *Container image pushing ${{
+                steps.push.outcome == 'failure' && 'failed completely' || 'succeeded with some retries'
+              }}* in
+              <${{ github.server_url }}/${{ github.repository }}/actions/runs/${{ github.run_id }}|GitHub Run>
+
+              ${{ steps.push.outputs.push_failures && format(
+                '*Failed targets:*\n• {0}', join(fromJson(steps.push.outputs.push_failures), '\n• ')
+              ) || '' }}