webhooks-and-events

name: webhooks-and-events description: "This skill should be used when the user is designing webhook systems, implementing webhook signing with HMAC-SHA256, building webhook retry logic, choosing event naming conventions, handling webhook ordering, implementing webhook endpoints, or building event-driven API integrations. Covers Stripe-style webhook patterns, signature verification, exponential backoff retries, and event deduplication." version: 1.0.0

Webhooks Are Promises You Must Keep

A webhook is a contract: when something happens on your platform, you will tell the subscriber about it reliably, securely, and in a format they can trust. Every failed delivery, every unsigned payload, every missing retry erodes that trust. Stripe delivers billions of webhook events with cryptographic verification, exponential backoff retries over a 72-hour window, and a structured event format that has become the industry standard. Your webhook system must meet the same bar.

The webhook producer carries the burden of proof. Consumers must be able to verify the event is authentic, handle duplicates gracefully, and trust that missed deliveries will be retried.

Event Naming: The resource.action Convention

Name every event type as resource.action, dot-separated, with the action in past tense. This is Stripe's convention and it has become the de facto standard across modern APIs.

order.created
order.updated
order.cancelled
payment.succeeded
payment.failed
payment.refunded
invoice.paid
invoice.overdue
invoice.finalized
customer.subscription.created
customer.subscription.updated
customer.subscription.deleted
customer.subscription.trial_will_end

Rules:

• Use dot-separated namespacing. Nested resources become parent.child.action (e.g., customer.subscription.created).
• Actions are always past tense. Something happened — you are reporting it. Use .created, .updated, .deleted, .succeeded, .failed. Never .create (that sounds like a command) or .creating (that implies in-progress).
• Use snake_case within segments when multiple words are needed: payment_intent.succeeded, not paymentIntent.succeeded.
• Maintain a canonical event type catalog. Document every event type your API can emit. Adding events is non-breaking; removing or renaming events is a breaking change.

Event Payload Structure

Every event follows the same envelope. Consumers parse one format regardless of the event type.

{
  "id": "evt_1NdBKYLkdIwHu7ixr0rMHeVX",
  "type": "order.created",
  "created": 1689956724,
  "api_version": "2024-01-15",
  "data": {
    "object": {
      "id": "ord_01HXK3GJ5V8WJKPT",
      "status": "pending",
      "total": 4999,
      "currency": "usd",
      "customer": "cus_NffrFeUfNV2Hib"
    },
    "previous_attributes": {}
  },
  "request": {
    "id": "req_abc123def456",
    "idempotency_key": "KG5LxwFBepaKHyKt"
  }
}

Required fields:

Design decisions:

• created is a Unix timestamp integer, not an ISO 8601 string. No timezone ambiguity.
• data.object contains the full resource snapshot, not a diff. Consumers reconstruct current state from a single event without fetching the API.
• previous_attributes is populated only for .updated events. Empty object otherwise.

Webhook Signing: HMAC-SHA256 with Timestamp

Sign every webhook payload with HMAC-SHA256. Include a timestamp in the signed content to prevent replay attacks. This is non-negotiable — an unsigned webhook endpoint is an open door for attackers to inject fake events.

The signature header:

X-Webhook-Signature: t=1689956724,v1=5257a869e7ecebeda32affa62cdca3fa51cad7e77a0e56ff536d0ce8e108d8bd

Signing algorithm (sender side):

1. Generate the current Unix timestamp.
2. Concatenate the timestamp and the raw JSON payload body with a dot separator: {timestamp}.{payload}.
3. Compute the HMAC-SHA256 of that string using the endpoint's signing secret.
4. Build the header: t={timestamp},v1={hex_signature}.

Verification algorithm (receiver side):

1. Parse t and v1 from the signature header.
2. Check that the timestamp is within the tolerance window (reject if older than 5 minutes).
3. Reconstruct the signed payload string: {t}.{raw_body}.
4. Compute the HMAC-SHA256 using the shared webhook secret.
5. Compare the computed signature to v1 using a constant-time comparison function.
6. If the comparison fails, reject with 400 Bad Request.

Critical implementation details:

• Always use constant-time comparison (crypto.timingSafeEqual in Node.js, hmac.compare_digest in Python). Standard string equality leaks timing information that attackers can exploit to reconstruct the signature byte by byte.
• Always verify against the raw request body bytes, not a re-serialized JSON object. JSON serialization is not deterministic — key ordering, whitespace, and Unicode escaping can differ between serializers, breaking the signature.
• The signing secret is per-endpoint, prefixed with whsec_ (e.g., whsec_test_51MqLiJLkdIwH). Return it only once, at endpoint creation time. If the consumer loses it, rotate and issue a new one.

Timestamp Validation: Replay Protection

The timestamp in the signature header prevents replay attacks. Without it, an attacker who intercepts a valid webhook payload can replay it days later and the signature will still verify.

Rule: Reject any event where the timestamp is more than 5 minutes old. This tolerance window accounts for clock skew between servers while keeping the replay window tight.

Attacker captures: t=1689956724,v1=abc123...
Replays 2 hours later.
Receiver: current_time - 1689956724 = 7200 seconds > 300 seconds
=> REJECTED

Five minutes is the standard tolerance. Stripe uses 300 seconds. If your infrastructure has exceptional clock skew, widen to 10 minutes but never more.

Retry Strategy: Exponential Backoff

When delivery fails — the endpoint returns a non-2xx status code, the connection times out, or DNS resolution fails — retry with exponential backoff. Do not drop events after a single failure.

Recommended retry schedule:

Attempt  1: Immediate
Attempt  2: 5 minutes
Attempt  3: 30 minutes
Attempt  4: 2 hours
Attempt  5: 8 hours
Attempt  6: 24 hours
Attempt  7: 48 hours
Final:      72 hours after first attempt

Rules:

• Add jitter to every retry delay (plus or minus 20%). Without jitter, all failed deliveries for a down endpoint retry simultaneously, creating a thundering herd that makes recovery harder.
• Set a 30-second timeout per delivery attempt. If the endpoint does not respond within 30 seconds, treat it as a failure and schedule the next retry.
• After exhausting all retries (72-hour window), mark the event as permanently failed. Send an email notification to the endpoint owner.
• If an endpoint fails consistently over multiple days, disable it automatically and notify the account owner. Do not silently continue retrying a dead endpoint indefinitely.
• Store every delivery attempt with its status code, response time, and error message. This history powers the delivery dashboard.

Idempotency: Consumers Must Handle Duplicates

Webhooks provide at-least-once delivery, never exactly-once. Network failures, retries, and edge cases mean the same event may arrive more than once. Every webhook consumer must be idempotent.

The pattern: Before processing an event, check if event.id has already been processed. If it has, return 200 OK without re-processing. Record the event ID within the same database transaction as the business logic to avoid race conditions.

Incoming event: evt_1NdBKYLkdIwHu7ixr0rMHeVX
  → Check processed_events table for this ID
  → Already exists? Return 200, skip processing
  → Not found? BEGIN transaction:
      1. INSERT into processed_events
      2. Execute business logic
      3. COMMIT
  → Return 200

The deduplication check and the business logic must happen atomically. If you check for duplicates, process the event, and then record the event ID as separate steps, a crash between steps 2 and 3 will cause the event to be re-processed on the next delivery.

Event Ordering: Do Not Rely on Arrival Order

Events may arrive out of order. A customer.subscription.updated event might arrive before the customer.subscription.created event if the first delivery attempt for created fails and is retried.

The pattern: Use the created timestamp to determine which event reflects the latest state. Implement a latest-wins strategy:

• Store last_event_timestamp alongside each resource.
• When processing an event, compare its created timestamp to the stored last_event_timestamp.
• If the incoming event is older, skip the update — a newer event has already been applied.
• Use upsert operations (insert-or-update) instead of separate create and update handlers. This handles any arrival order gracefully.

Event A (created: 1000): customer.subscription.created  → arrives second
Event B (created: 1001): customer.subscription.updated  → arrives first

Processing B first: upsert with last_event_timestamp = 1001
Processing A second: created = 1000 < last_event_timestamp = 1001 → skip

This eliminates the brittle assumption that created always arrives before updated. Build your handlers to work regardless of event order.

Webhook Endpoint Requirements

For webhook producers (your API):

• Set a 30-second timeout per delivery. If the consumer does not respond, treat it as a failure.
• Accept any 2xx status code as successful delivery. Do not require exactly 200.
• Ignore the response body. Webhook delivery is fire-and-forget after a successful status code.

For webhook consumers (your users):

• Respond with 200 OK within 5 seconds. Return immediately, then process the event asynchronously using a background job queue.
• Never perform long-running work synchronously in the handler. If processing takes 25 seconds and the producer times out at 30, one slow query triggers unnecessary retries.
• Use the raw request body for signature verification, not a parsed-and-re-serialized object.

Webhook Registration API

Let consumers register endpoints via your API and filter which event types they receive. Do not require manual configuration in a dashboard.

POST /v1/webhook_endpoints
{
  "url": "https://example.com/webhooks",
  "enabled_events": ["order.created", "payment.succeeded", "payment.failed"],
  "description": "Production payment events"
}

→ 201 Created
{
  "id": "wh_1MqVTHLkdIwHu7ix5RbKdAnA",
  "url": "https://example.com/webhooks",
  "status": "enabled",
  "enabled_events": ["order.created", "payment.succeeded", "payment.failed"],
  "secret": "whsec_live_abc123...",
  "created": 1689956724
}

Rules:

• Return the signing secret only on creation. Never return it on subsequent GET or LIST requests.
• Support enabled_events filtering. A consumer processing only payments should not receive order events.
• Support a wildcard ["*"] to subscribe to all event types.
• Provide CRUD operations: create, list, retrieve, update, and delete endpoints.
• Include a status field (enabled / disabled) that reflects whether the endpoint is active.
• Expose an events API (GET /v1/events) that lets consumers list recent events for debugging, with filters by type and date range.

Monitoring and Observability

A webhook system without monitoring is a black hole. Build these from day one:

Delivery dashboard. Show every delivery attempt for every endpoint: timestamp, event type, HTTP status code, response time, and whether it was a retry. Let consumers see their own endpoint's delivery history.

Failure alerts. When an endpoint accumulates consecutive failures (e.g., 5 in a row), send an email alert to the owner. Do not wait until the 72-hour retry window expires.

Manual replay. Provide a dashboard button and an API endpoint (POST /v1/events/:id/retry) to re-trigger delivery of a specific event. Replays recover data after consumer bug fixes.

Metrics. Track delivery success rate, p95 response time, retry rate, and failure rate per endpoint. Use these for automatic endpoint disabling decisions.

Examples

Working implementations in examples/:

• examples/webhook-signature-verification.md -- Complete HMAC-SHA256 webhook signature generation (sender) and verification (receiver) with timestamp validation in Node.js and Python
• examples/webhook-retry-system.md -- Webhook delivery system with exponential backoff, dead letter queue, and delivery status tracking in Node.js and Python

Review Checklist

When reviewing or building webhook systems:

• Every event type follows the resource.action naming convention with past-tense actions
• Event payloads use the standard envelope: id, type, created, data.object, request
• All payloads are signed with HMAC-SHA256 using a per-endpoint secret
• Signature includes a timestamp and verification rejects events older than 5 minutes
• Signature comparison uses constant-time equality, never standard string comparison
• Failed deliveries retry with exponential backoff up to 72 hours with jitter
• Endpoints that fail consistently are automatically disabled with owner notification
• Webhook handlers are idempotent — duplicate events are detected by event.id and skipped
• Event ordering is handled via timestamp comparison, not arrival order assumptions
• Consumers respond within 5 seconds and process events asynchronously
• The registration API supports event type filtering and returns the signing secret only at creation
• A delivery dashboard with manual replay is available for debugging failed deliveries