How to Retry Failed Stripe Webhooks (The Right Way)

A customer just emailed you: "I paid for the upgrade, but my account is still on the Free Plan."

You check your logs. Nothing. You check Stripe. The payment succeeded, but the webhook showing checkout.session.completed failed with a 500 Error because your server was deploying code at that exact second.

Now you need to "replay" that event to give the customer their access. Here are the three ways to do it.

Method 1: The Stripe Dashboard (Manual)

This is fine for fixing one single error, but painful for bulk failures.

1. Log in to your Stripe Dashboard.
2. Go to Developers > Webhooks.
3. Click on your endpoint URL.
4. Filter by "Failed".
5. Click the specific event ID (e.g., evt_1J2k...).
6. Click the "Resend" button in the top right.

The Downside: You cannot "Select All" and retry. If you had 2 hours of downtime and missed 500 events, you have to click that button 500 times.

Method 2: The Stripe CLI (For Developers)

If you are comfortable with the terminal, you can use the Stripe CLI to resend an event. This is useful for testing local development logic.

stripe events resend evt_1Mk92J2eZvKYlo2C0Y1

However, this requires you to find the Event IDs first. You'd likely need to write a script to fetch failed event IDs via the API and then loop through them to trigger resends.

Method 3: The "Set and Forget" Way (WebHookGuard)

The problem with the first two methods is that they require manual intervention. You have to notice the failure, find the ID, and trigger the retry.

A better architecture is to use a Middleware Buffer.

How it works:

• Step 1: Point Stripe to your WebHookGuard URL instead of your server.
• Step 2: WebHookGuard accepts the event instantly (Stripe sees a 200 OK).
• Step 3: WebHookGuard tries to forward it to your server.
• Step 4: If your server fails (500 error), WebHookGuard automatically retries on a schedule (1s, 5s, 1m, 1h).

Handling Idempotency

When you replay webhooks, you must ensure you don't process the same payment twice (double credit). This is called Idempotency.

Always check if you have already processed an Event ID before running your logic:

async function handleWebhook(event) {
  const exists = await db.processedEvents.find({ id: event.id });
  
  if (exists) {
    return res.status(200).send('Already processed');
  }

  // Run business logic...
  
  await db.processedEvents.create({ id: event.id });
}