diff --git a/.github/workflows/lychee.yml b/.github/workflows/lychee.yml
index 696d160004..72cf3fa499 100644
--- a/.github/workflows/lychee.yml
+++ b/.github/workflows/lychee.yml
@@ -15,7 +15,7 @@ jobs:
     steps:
       - uses: actions/checkout@v4
 
-      - name: 🍈 Lychee Link Checker
+      - name: 🍈 Lychee Link Checker (First Run)
         id: lychee
         uses: lycheeverse/lychee-action@v2
         with:
@@ -23,6 +23,7 @@ jobs:
           output: ../lychee/out.md
           args: >
             --cache
+            --cache-exclude-status 429,500,502,503,504
             --max-cache-age 5m
             --verbose
             --no-progress
@@ -39,23 +40,58 @@ jobs:
         env:
           GITHUB_TOKEN: ${{ secrets.github_token }}
 
+      - name: 🔄 Retry Lychee Link Checker (Second Run for Timeouts)
+        id: lychee-retry
+        if: ${{ always() && steps.lychee.outputs.exit_code != 0 }}
+        uses: lycheeverse/lychee-action@v2
+        with:
+          fail: false
+          output: ../lychee/out-retry.md
+          args: >
+            --cache
+            --max-cache-age 5m
+            --verbose
+            --no-progress
+            --accept 200,201,204,304,403,429
+            --cache-exclude-status 429,500,502,503,504
+            --timeout 30
+            --max-retries 10
+            --retry-wait-time 10
+            --exclude 'http://localhost.*'
+            --exclude 'https://localhost.*'
+            --exclude 'https://cockroachlabs.com'
+            --exclude '^/.*'
+            './**/*.md' './**/*.mdx'
+          workingDirectory: "content"
+        env:
+          GITHUB_TOKEN: ${{ secrets.github_token }}
+
       - name: 📝 Clean up Lychee Report
         if: ${{ always() && github.event.pull_request.head.repo.fork == false }}
         run: |
-          if [ -f "lychee/out.md" ]; then
+          # Use retry results if available, otherwise use first run results
+          if [ -f "lychee/out-retry.md" ]; then
+            REPORT_FILE="lychee/out-retry.md"
+            NOTE="Links are cached for 5 minutes. Failed links (timeouts, rate limits) are retried in a second run with longer timeout."
+          elif [ -f "lychee/out.md" ]; then
+            REPORT_FILE="lychee/out.md"
+            NOTE="Links are cached for 5 minutes to avoid unnecessary requests, and speed up consecutive runs."
+          fi
+
+          if [ -n "$REPORT_FILE" ]; then
             # Read the original output
-            ORIGINAL=$(cat lychee/out.md)
-            
+            ORIGINAL=$(cat "$REPORT_FILE")
+
             # Create formatted output
-            cat > lychee/formatted.md << 'EOF'
+            cat > lychee/formatted.md << EOF
           ## 🍈 Lychee Link Check Report
 
-          > **Note:** Links are cached for 5 minutes to avoid unnecessary requests, and speed up consecutive runs.
+          > **Note:** $NOTE
 
           ### 📊 Results Overview
 
           EOF
-            
+
             # Append the original content with title replacement
             echo "$ORIGINAL" | sed 's/^# Summary$//' | sed 's/^## Summary$//' >> lychee/formatted.md
           fi
@@ -68,5 +104,12 @@ jobs:
           body-path: lychee/formatted.md
 
       - name: 🚫 Fail if broken links found
-        if: ${{ steps.lychee.outputs.exit_code != 0 }}
-        run: exit ${{ steps.lychee.outputs.exit_code }}
+        if: ${{ steps.lychee-retry.conclusion == 'success' && steps.lychee-retry.outputs.exit_code != 0 || steps.lychee-retry.conclusion == 'failure' }}
+        run: |
+          if [ "${{ steps.lychee-retry.conclusion }}" == "success" ]; then
+            echo "Failing based on retry run results"
+            exit ${{ steps.lychee-retry.outputs.exit_code }}
+          else
+            echo "Failing based on first run results"
+            exit ${{ steps.lychee.outputs.exit_code }}
+          fi