Why webhook reliability is harder than it looks

Webhooks are often treated as a simple HTTP problem:

One service sends a request, another service returns 200 OK.

But once webhooks affect payments, orders, subscriptions, CRM updates, or customer access, the actual problem becomes much larger.

A webhook can be lost because of a temporary outage, a deployment issue, an expired TLS certificate, a database problem, or an infrastructure migration.

And migrations can create the opposite issue too.

For example, after changing a DNS record, some webhook senders may still use the old IP address while others already reach the new server. If both servers are active, the same event may be processed twice. If the old server is gone, some events may fail entirely.

That means reliable webhook handling needs to account for both:

• events that do not arrive;

• events that arrive more than once.

The usual answer is an at-least-once delivery model combined with idempotent processing on the receiving side.

In practical terms:

• retry failed deliveries;

• store events durably before doing expensive work;

• use event IDs or idempotency keys;

• make duplicate processing safe;

• keep delivery history;

• provide a way to replay events when something fails.

This is one of the reasons Adal Cloud focuses on retained requests, delivery visibility, retries, and replay rather than treating a webhook as a one-shot request.

A reliable webhook system is not just one that can send requests. It is one that helps teams understand what happened when delivery does not go as planned.

We published a deeper technical breakdown here:

https://adal.cloud/blog/2026-06-29-what-does-losing-a-webhook-mean

How does your team currently handle webhook retries and duplicate events?

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