Why Webhooks Still Fail Us in 2026 and How We Can Do Better

[Carsten17]

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We've spent the last few months integrating with multiple providers’ webhooks (payments, scheduling, AI APIs, automation tools), and the pattern is depressingly consistent.

Events arrive late or not at all. Providers give almost no visibility into what actually happened. Auth and configuration errors are opaque and only become “correct” after painful trial and error.

This isn’t about one vendor; it feels systemic across a lot of “modern” APIs.

What keeps breaking in practice without HookVerify
Delayed or missing webhooks. Events show up minutes or hours late, or never arrive, even though the provider claims the event was sent successfully. Empty or partial payloads: the webhook fires but the body is empty or missing key fields unless the client polls the API afterward. Opaque errors: generic “invalid API key” / “webhook failed” messages with no clear indication of which header/key was wrong, whether DNS/SSL/WAF/rate limits were involved, or whether retries are happening. Infra getting in the way – CDNs/WAFs/bot protections randomly block webhook traffic so it never reaches application code.

What “good” would look like
Reliability – at-least-once delivery, documented retry behavior and backoff, clear maximum retry window, and strong idempotency (stable event IDs, recommended idempotency keys). Observability: UI and API to inspect individual webhook events and every delivery attempt (timestamp, status code, error, latency), plus the ability to search and replay events for a destination and time window. Actionable errors: clear separation between auth problems, destination issues, and provider-side incidents/rate limits, with docs that actually match how setup and scopes work. Developer-friendly testing: built-in “send test event” and “webhook inspector”, with good guidance for local tunneling/sandbox setups.

What I’d like from this discussion
For people building or operating webhook systems (GitHub staff, app authors, integrators):
Which reliability/observability features have helped your users the most?
Any public “gold standard” implementations you point teams to?
If you maintain a webhook provider, what’s been hardest about delivering these guarantees?

If there’s interest, I’d like to turn the responses into a shared checklist/reference for webhook design and reviews.

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