Based on the research and your specific situation, here's what's happening and what you should check: 1. How Retry Should Work: - When you click "Retry" in the UI, Prefect creates a new flow run with the same parameters as the failed run - This new run should be picked up by an available worker that matches the deployment's work pool - The flow should then start executing relatively quickly (usually within seconds to a minute) 2. If it's hanging for 20 minutes, this suggests several possible issues: a. Worker Issues: - Verify that your workers are running and healthy in your Kubernetes cluster - Check worker logs for any errors or issues - Ensure workers are properly connected to your work pool

bash
   kubectl logs -n your-namespace -l app=prefect-worker

b. Work Pool Configuration: - Verify that the work pool is properly configured and matches your deployment - Check that the work pool type matches your infrastructure (kubernetes) c. Infrastructure Issues: - Check if there are any resource constraints in your Kubernetes cluster - Verify network connectivity between your worker and Prefect server - Ensure there are no pending pods or resource quotas preventing new flow runs 3. Troubleshooting Steps: 1. Check the Prefect UI for any error messages in the flow run logs 2. Verify worker health:

bash
      kubectl get pods -n your-namespace -l app=prefect-worker

3. Check worker logs for connection issues or errors 4. Verify that your work pool is properly configured for Kubernetes 5. Try stopping and restarting the worker pods to refresh the connection 4. Common Solutions: - If workers are unresponsive, restart them - If the issue persists, try creating a new work pool and updating your deployment to use it - Check that your Helm chart values are correctly configured, especially regarding worker connections to the Prefect server Would you like me to help you investigate any specific aspect of these potential issues? It would be helpful to know: 1. Can you see any error messages in the UI for the hanging flow run? 2. Are other flow runs working correctly, or is this issue affecting all retries? 3. Can you confirm if your workers are showing as "ONLINE" in the UI?