Based on the research and available information, here's what we know and what you should check: 1. Check the Event Feed First - In Prefect Cloud, go to the Event Feed and look for events with the type 'prefect-cloud.webhook.failed' - This will show if the webhooks are being triggered but failing to deliver 2. Verify Webhook Configuration - Check if the webhook is properly configured in Prefect Cloud - Verify that the service account assigned to the webhook (if any) has the correct permissions 3. Check Receiving System - The 15-minute delay suggests there might be an issue with the system receiving the webhooks - Check if the receiving system has any rate limiting, queuing, or processing delays - Verify that the receiving system's logs show when it actually receives the webhook 4. Network and Infrastructure - Check for any network latency issues between Prefect Cloud and your receiving system - Verify there are no proxy or firewall rules causing delays To debug this effectively, I recommend: 1. First, confirm in the Prefect Cloud Event Feed that the webhook events are being triggered immediately when the flow run status changes 2. Check the webhook configuration in Prefect Cloud for any error events 3. Add logging on your receiving system to timestamp exactly when the webhook is received 4. Compare the timestamps between: - When the flow run status changes - When Prefect Cloud sends the webhook (from Event Feed) - When your system receives the webhook Could you check the Event Feed and let me know if you see any webhook failure events or if the timestamps there match what you're expecting? This will help narrow down where in the chain the delay is occurring.

Based on the research and your specific situation, here's what's likely happening: 1. Root Cause: In a self-hosted environment, there's likely an issue with the event processing service or scheduler that's causing the delay. The fact that you see the delay in the event feed itself (rather than in webhook delivery) points to this being an internal timing issue. 2. Specific Components to Check: a. Scheduler Service: Check the logs for your Prefect scheduler service. Look for warnings about tasks taking longer than their loop intervals or any timeout errors. b. Database Performance: Check if there are any delays in database operations, as this can cause cascading delays in event processing. c. Event Processing Configuration: The event processing service has certain intervals at which it checks for and processes events. 3. Recommended Debugging Steps: 1. Check your Prefect server logs for any warnings about services taking longer than their loop intervals 2. Monitor your database performance during these delays 3. Check the resource usage (CPU/Memory) of your Prefect services 4. Verify the timestamps in your database for: - When the flow run status actually changes - When the automation event is created - When the automation is triggered Could you share: 1. Are you running the latest version of Prefect? 2. Can you check your server logs for any warnings about service delays or timeouts? 3. Is this happening for all automations or just specific ones? This information would help us narrow down the exact cause and provide more specific solutions.