diff --git a/.github/workflows/push.yml b/.github/workflows/push.yml
index 4b89edcd0..499bfc75c 100644
--- a/.github/workflows/push.yml
+++ b/.github/workflows/push.yml
@@ -72,6 +72,30 @@ jobs:
       - name: Set up GCloud
         uses: "google-github-actions/setup-gcloud@v2"
       - name: Deploy
+        id: deploy
+        run: make deploy
+        env:
+          POLICYENGINE_DB_PASSWORD: ${{ secrets.POLICYENGINE_DB_PASSWORD }}
+          GOOGLE_APPLICATION_CREDENTIALS: ${{ secrets.GCP_SA_KEY }}
+          POLICYENGINE_GITHUB_MICRODATA_AUTH_TOKEN: ${{ secrets.POLICYENGINE_GITHUB_MICRODATA_AUTH_TOKEN }}
+          ANTHROPIC_API_KEY: ${{ secrets.ANTHROPIC_API_KEY }}
+          OPENAI_API_KEY: ${{ secrets.OPENAI_API_KEY }}
+          HUGGING_FACE_TOKEN: ${{ secrets.HUGGING_FACE_TOKEN }}
+        continue-on-error: true
+      - name: Retry Deploy (1st attempt)
+        if: steps.deploy.outcome == 'failure'
+        id: retry1
+        run: make deploy
+        env:
+          POLICYENGINE_DB_PASSWORD: ${{ secrets.POLICYENGINE_DB_PASSWORD }}
+          GOOGLE_APPLICATION_CREDENTIALS: ${{ secrets.GCP_SA_KEY }}
+          POLICYENGINE_GITHUB_MICRODATA_AUTH_TOKEN: ${{ secrets.POLICYENGINE_GITHUB_MICRODATA_AUTH_TOKEN }}
+          ANTHROPIC_API_KEY: ${{ secrets.ANTHROPIC_API_KEY }}
+          OPENAI_API_KEY: ${{ secrets.OPENAI_API_KEY }}
+          HUGGING_FACE_TOKEN: ${{ secrets.HUGGING_FACE_TOKEN }}
+        continue-on-error: true
+      - name: Retry Deploy (2nd attempt)
+        if: steps.retry1.outcome == 'failure'
         run: make deploy
         env:
           POLICYENGINE_DB_PASSWORD: ${{ secrets.POLICYENGINE_DB_PASSWORD }}
diff --git a/changelog_entry.yaml b/changelog_entry.yaml
index e69de29bb..7fa89061a 100644
--- a/changelog_entry.yaml
+++ b/changelog_entry.yaml
@@ -0,0 +1,4 @@
+- bump: patch
+  changes:
+    added:
+      - GitHub action automated retry