/stripe-health - Stripe Webhook Health Check

Run a comprehensive diagnostic on Stripe webhook integration.

When to Use

• Before deploying changes to webhook handlers
• When subscription sync issues are reported
• After configuring new webhook endpoints
• As part of incident investigation

Diagnostic Steps

1. Check Webhook Endpoints

# List all webhook endpoints for this project
stripe webhook_endpoints list --api-key "$STRIPE_SECRET_KEY" 2>&1 | jq '.data[] | {id, url, status, enabled_events}'

Red flags:

• Multiple endpoints for same URL (duplicate signing secrets)
• Status != "enabled"
• Missing critical events (checkout.session.completed, customer.subscription.*)

2. Check for Redirects (CRITICAL)

# Get the webhook URL from endpoints, then check for redirects
WEBHOOK_URL=$(stripe webhook_endpoints list --api-key "$STRIPE_SECRET_KEY" 2>&1 | jq -r '.data[0].url')
echo "Testing: $WEBHOOK_URL"
curl -s -I -X POST "$WEBHOOK_URL" 2>&1 | head -5

Red flags:

• HTTP 307/308/301/302 = REDIRECT = Stripe won't deliver webhooks
• Must return 4xx or 5xx, NOT 3xx

3. Check Recent Event Delivery

# Check last 5 events and their pending_webhooks count
stripe events list --limit 5 --api-key "$STRIPE_SECRET_KEY" 2>&1 | jq '.data[] | {id, type, created: (.created | todate), pending_webhooks}'

Red flags:

• pending_webhooks > 0 for old events = delivery failing
• pending_webhooks should decrease over time

4. Check for Failed Deliveries

# Look for events with high pending_webhooks (failures)
stripe events list --limit 20 --api-key "$STRIPE_SECRET_KEY" 2>&1 | jq '[.data[] | select(.pending_webhooks > 0)] | length'

Red flags:

• More than 2-3 events with pending_webhooks > 0

5. Test Live Delivery

# Resend a recent event and watch logs
RECENT_EVENT=$(stripe events list --limit 1 --type checkout.session.completed --api-key "$STRIPE_SECRET_KEY" 2>&1 | jq -r '.data[0].id')
ENDPOINT_ID=$(stripe webhook_endpoints list --api-key "$STRIPE_SECRET_KEY" 2>&1 | jq -r '.data[0].id')

echo "Resending $RECENT_EVENT to $ENDPOINT_ID..."
stripe events resend "$RECENT_EVENT" --webhook-endpoint "$ENDPOINT_ID" --api-key "$STRIPE_SECRET_KEY"

echo ""
echo "Watch Vercel logs for delivery confirmation..."
echo "Run: vercel logs your-app --json | grep webhook"

Health Report Format

STRIPE WEBHOOK HEALTH CHECK
===========================
Endpoints: [count] configured
  - [url] (status: [enabled/disabled])

Redirect Check: [PASS/FAIL]
  - [url] returns [status code]

Recent Delivery: [PASS/WARN/FAIL]
  - [X] events with pending_webhooks > 0

Recommendation: [action if any issues found]

Common Issues & Fixes

| Symptom | Likely Cause | Fix | |---------|--------------|-----| | pending_webhooks stays high | Redirect or wrong URL | curl -I the URL, update to canonical domain | | Duplicate endpoints | Created endpoint twice | Delete older one, keep one with matching secret | | Events not appearing | Wrong events enabled | Update endpoint to include required events | | Signature verification fails | Wrong secret in env | Get secret from Stripe dashboard, update env |