Why Stripe Retries Your Webhooks (And When to Worry)#

Scope: This guide focuses specifically on Stripe’s webhook retry behavior and handling duplicate deliveries. For a comprehensive overview, see the Complete Guide to Stripe Webhooks in Next.js.

Stripe webhook retry becomes relevant once your application depends on reliably processing payment events. Initially, webhooks usually work fine—Stripe sends events, your API route processes them, and everything appears to function correctly. The complexity emerges when deliveries fail, timeout, or require replay after fixes.

Eventually, you find yourself debugging webhook deliveries through Stripe’s dashboard, checking logs for processing errors, and manually triggering retries when events don’t arrive as expected. The handler itself becomes something you’d prefer not to touch, knowing that changes might break the delicate balance between Stripe’s retry behavior and your application logic.

When this keeps happening, it’s usually less about handler logic and more about missing persistence and visibility between Stripe and your app.

Why Stripe webhook retries become difficult to debug#

Stripe’s retry mechanism operates independently of your application’s internal processing. When your endpoint returns a 200 status, Stripe considers the delivery successful, regardless of whether your business logic actually completed. This creates several production scenarios that are hard to diagnose:

Webhook deliveries that appear successful in Stripe’s dashboard but never updated your database. Retries that process the same event multiple times because your idempotency logic didn’t account for partial failures. Timeouts during database operations that cause Stripe to retry, but your application has no record of the original attempt.

Failed signature verification that returns 400, triggering Stripe’s retry schedule, but your logs only show the verification failure without context about the retry sequence. Events that arrive out of order due to retries, making it difficult to maintain consistent state in your application.

If this is a low-volume app where occasional missed payment events are acceptable, this complexity may not matter yet.

Why this is tricky in Next.js specifically#

Next.js API routes run in a serverless execution model where each request is handled independently. This means your webhook handler has no memory of previous attempts, making it difficult to track retry patterns or maintain processing state across deliveries.

The request lifecycle in Next.js is designed to be stateless, which works well for most HTTP requests but creates challenges for webhook processing. When Stripe retries a webhook, your API route treats it as a completely new event, with no awareness that it might be processing the same data again.

Serverless environments also have execution time limits that can cause timeouts during complex webhook processing. If your handler needs to perform multiple database operations or call external APIs, a timeout can leave your application in an inconsistent state while Stripe marks the delivery as failed and schedules a retry.

How HookRelay helps with Stripe webhook retries#

HookRelay acts as a buffer between Stripe and your Next.js application, handling the reliability concerns that make webhook retry logic complicated. Instead of Stripe retrying your API route directly, it retries HookRelay, which then manages the delivery to your application with full visibility into each attempt.

This separation means your Next.js handler can focus on processing the webhook data rather than managing delivery reliability. HookRelay tracks delivery attempts and failures outside your application’s request cycle, providing a clear view of what happened during each retry attempt.

When processing fails, you can inspect the exact payload and error details, fix your handler, and replay the event without waiting for Stripe’s next retry attempt. The retry logic and failure recovery happen in infrastructure designed for that purpose, rather than being mixed into your application code.

What this looks like in a Next.js app#

• Configure Stripe to send webhooks to a HookRelay endpoint instead of your API route
• HookRelay verifies Stripe signatures and forwards events to your Next.js application
• Each delivery attempt is recorded with timestamps, response codes, and error details
• Failed events remain available for inspection and replay after you fix processing issues
• Your API route receives events through HookRelay but processes them normally

Stripe-specific considerations#

Stripe’s webhook retry schedule follows an exponential backoff pattern, with attempts spread over several days. This means a processing failure might not surface until much later, making it difficult to correlate the failure with recent code changes.

Stripe also requires signature verification using your webhook endpoint secret. HookRelay handles this verification step, ensuring that only legitimate Stripe events reach your application while providing visibility into any signature failures.

For idempotency, Stripe recommends using the event ID to prevent duplicate processing. With HookRelay, you can see the complete delivery history for each event ID, making it easier to implement and debug idempotency logic.

When this approach makes sense#

This pattern becomes useful once webhook processing is operationally important to your application. If payment events need to reliably trigger user account updates, subscription changes, or other critical business logic, having visibility and replay capabilities reduces the operational overhead.

For early-stage applications or prototypes where webhook processing failures can be handled manually, the additional infrastructure complexity might not be worth the benefits.

Persistent webhook infrastructure#

Rather than treating webhook reliability as a development problem to solve in your Next.js API routes, HookRelay handles it as an infrastructure concern. Your application receives events reliably, and you can debug processing issues without navigating Stripe’s retry schedule or guessing what happened during failed deliveries.

See how webhook retries and failures are recorded for the technical details of delivery tracking and replay.