diff --git a/.github/workflows/docs-sync-auto-troubleshooting.yml b/.github/workflows/docs-sync-auto-troubleshooting.yml
new file mode 100644
index 00000000000..e439c1649ee
--- /dev/null
+++ b/.github/workflows/docs-sync-auto-troubleshooting.yml
@@ -0,0 +1,72 @@
+# Sync AI-generated troubleshooting guides from supabase/troubleshooting
+
+name: Sync from supabase/troubleshooting
+
+on:
+  repository_dispatch:
+    types: [sync_from_upstream]
+  workflow_dispatch:
+
+permissions:
+  contents: write
+  pull-requests: write
+
+jobs:
+  sync:
+    runs-on: ubuntu-latest
+
+    steps:
+      - name: Checkout supabase/supabase
+        uses: actions/checkout@08eba0b27e820071cde6df949e0beb9ba4906955 # v4.3.0
+        with:
+          persist-credentials: true
+
+      - name: Decode the GitHub App Private Key
+        id: decode
+        run: |
+          private_key=$(echo "${{ secrets.DOCS_GITHUB_APP_PRIVATE_KEY }}" | base64 --decode | awk 'BEGIN {ORS="\\n"} {print}' | head -c -2) &> /dev/null
+          echo "::add-mask::$private_key"
+          echo "private-key=$private_key" >> "$GITHUB_OUTPUT"
+
+      - name: Create GitHub App token for supabase/troubleshooting
+        id: app-token
+        uses: actions/create-github-app-token@67018539274d69449ef7c02e8e71183d1719ab42 # v2.1.4
+        with:
+          app-id: ${{ vars.DOCS_GITHUB_APP_ID }}
+          private-key: ${{ steps.decode.outputs.private-key }}
+          repositories: troubleshooting
+          permission-contents: read
+
+      - name: Checkout supabase/troubleshooting
+        uses: actions/checkout@08eba0b27e820071cde6df949e0beb9ba4906955 # v4.3.0
+        with:
+          persist-credentials: false
+          token: ${{ steps.app-token.outputs.token }}
+          repository: supabase/troubleshooting
+          path: troubleshooting-upstream
+
+      - name: Sync supabase/troubleshooting changes back to supabase/supabase
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+        run: |
+          git config user.name 'github-docs-bot'
+          git config user.email 'github-docs-bot@supabase.com'
+          BRANCH_NAME="bot/sync-troubleshooting"
+          EXISTING_BRANCH=$(git ls-remote --heads origin $BRANCH_NAME)
+          if [[ -n "$EXISTING_BRANCH" ]]; then
+              git push origin --delete $BRANCH_NAME
+          fi
+          git checkout -b $BRANCH_NAME
+          rsync --archive --verbose --ignore-existing ./troubleshooting-upstream/guides/ ./apps/docs/content/troubleshooting/
+          git add apps/docs/content/troubleshooting/
+          if git diff --quiet --cached; then
+            echo "No changes to sync"
+            exit 0
+          fi
+          git commit --message "Sync from supabase/troubleshooting"
+          git push origin $BRANCH_NAME
+          if gh pr list --state open --head $BRANCH_NAME --json number --jq '.[0].number' | grep -q .; then
+            gh pr comment "$BRANCH_NAME" --body "Updated troubleshooting sync with latest changes."
+          else
+            gh pr create --title "[bot] Sync from supabase/troubleshooting" --body "This PR syncs the latest troubleshooting guides from the supabase/troubleshooting repository." --head $BRANCH_NAME
+          fi