Prompt

debug webhook 500 errors

Technology / API Platforms1 observationLast seen Oct 5, 2026

Latest observation

Oct 5, 2026OpenAI APIWeb search: off

To debug webhook 500 errors, I’d approach it in this order:

  1. 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.
  2. 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
  3. 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"}'
      
  4. 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
  5. Check authentication/signature verification

    • If you validate HMAC/signatures, failures sometimes get handled poorly and turn into 500s.
    • These should usually return 401 or 400, not 500.
  6. 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
  7. Make the handler fail safely

    • Return explicit errors for bad input instead of throwing uncaught exceptions.
    • Example patterns:
      • 400 for malformed payloads
      • 401/403 for auth/signature issues
      • 500 only for unexpected server faults
  8. 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.

If you want, paste:

  • the webhook handler code,
  • one failing payload,
  • and the stack trace/log output,

and I can help pinpoint the 500.

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