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Engineer Webhook Delivery Guarantee with Dead Letter Queue for Failed Events #601

@temma02

Description

@temma02

Description

Implement a webhook delivery guarantee system with a dead letter queue that captures and enables reprocessing of webhook events that fail to process after exhausting retries.

Requirements and Context

  • Reliability: No webhook event should be silently lost
  • Testing: Test DLQ capture and reprocessing
  • Documentation: Document the DLQ workflow

Suggested Execution

Branch: feat/issue-065-webhook-dead-letter-queue

Implement Changes

  • Add a dead letter store for webhook events that exhaust retries
  • Capture the full event payload and failure reason in the DLQ
  • Add an admin endpoint to inspect and reprocess DLQ entries
  • Apply DLQ handling to both Stripe and GitHub webhook processors

Test and Commit

  • Test that failed events land in the DLQ after retry exhaustion
  • Test reprocessing of a DLQ entry
  • Document the DLQ workflow

Example Commit Message

feat(webhooks): add dead letter queue for failed webhook events

- Capture failed events with payload and failure reason
- Add admin endpoint for DLQ inspection and reprocessing
- Apply DLQ handling to Stripe and GitHub webhooks

Guidelines

  • Store the full original payload for accurate reprocessing
  • Protect the DLQ admin endpoint with proper authorization
  • Avoid infinite reprocessing loops

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