Prompt
debug webhook 500 errors
Latest observation
Oct 5, 2026
OpenAI APIWeb search: off
To debug webhook 500 errors, I’d approach it in this order:
-
Check the webhook receiver logs
- Look at the server/app logs for the exact exception, stack trace, and request payload.
- A 500 means the error is on your side, so the logs usually tell you the real cause.
-
Verify the incoming request
- Confirm headers, method, and body match what your endpoint expects.
- Common issues:
- Invalid JSON
- Missing required fields
- Wrong
Content-Type - Unexpected signature/auth format
-
Reproduce locally
- Send the same payload with
curl, Postman, or a test script. - Example:
curl -X POST https://your-webhook-url \ -H "Content-Type: application/json" \ -d '{"test":"value"}'
- Send the same payload with
-
Inspect payload handling
- Make sure your code safely parses the body.
- Add guards around:
- JSON decoding
- nil/undefined fields
- type mismatches
- array vs object assumptions
-
Check authentication/signature verification
- If you validate HMAC/signatures, failures sometimes get handled poorly and turn into 500s.
- These should usually return
401or400, not500.
-
Look for timeouts or downstream failures
- If your webhook handler calls databases, APIs, or queues:
- test those dependencies
- check for connection errors
- confirm timeouts aren’t too short
- If your webhook handler calls databases, APIs, or queues:
-
Make the handler fail safely
- Return explicit errors for bad input instead of throwing uncaught exceptions.
- Example patterns:
400for malformed payloads401/403for auth/signature issues500only for unexpected server faults
-
Add better observability
- Log:
- request ID / correlation ID
- event type
- payload size
- parsing/auth failures
- If possible, store failed payloads in a dead-letter queue or error store for replay.
- Log:
If you want, paste:
- the webhook handler code,
- one failing payload,
- and the stack trace/log output,
and I can help pinpoint the 500.