The Tool Desk
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Start by identifying which stage failed
A billing-to-license webhook flow has several distinct stages: the provider generates an event, routes it to a configured endpoint, your server accepts it, and your application applies the resulting license change. A problem at any stage can look like “the webhook didn’t arrive.”
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- No event in provider history: Check whether the relevant event was generated, whether the endpoint is configured for it, and whether you are looking at the correct test, sandbox, or live environment.
- Event exists, but no successful attempt: Inspect the destination URL, attempt status, response code, response body, and endpoint logs for connectivity, TLS, timeout, or server errors.
- Successful response, but no license change: Check whether the receiver durably saved or queued the event and whether the background processor completed it.
- License changed more than once or reverted: Look for duplicate delivery or events processed out of order.
Use the provider’s delivery record and your own application logs together. Correlate them with the provider’s stable event identifier and the affected subscription or license. Stripe’s support guidance, for example, directs operators to the endpoint’s failed attempts and the details of an individual attempt: Stripe webhook troubleshooting.
Why didn’t my license webhook arrive?
Verify the endpoint and event subscription
Confirm the endpoint exists, points to the intended public callback URL, and is subscribed to the event that represents the actual lifecycle change. Check the provider’s event catalog rather than guessing names: creation, renewal, cancellation, expiration, payment failure, and license update may be separate events.
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Lemon Squeezy lists webhook event types, including license-key and subscription events, and recommends subscribing to license_key_created when licenses are enabled. Its documentation also describes test-mode event simulation. See Lemon Squeezy’s webhook guide and webhook event types.
Check the environment and provider history
Make sure the event was generated in the same environment you are inspecting. A test or sandbox event will not necessarily appear in a live account’s delivery history, or vice versa. Search the provider’s event or notification log by the relevant object and time. If the event is absent, investigate event generation, filters, destination configuration, and environment selection before debugging your receiver.
If the event exists, note its type, destination, attempt time, status, response code, and response body. An attempt record is evidence that the provider tried to deliver; it is not evidence that your application successfully processed the license change.
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Why was the webhook rejected or marked failed?
Check reachability, HTTP handling, and signatures
Verify that the callback URL is publicly reachable, accepts the provider’s expected HTTP method and content type, and can respond without exceeding the provider’s deadline. Inspect server, proxy, and load-balancer logs at the exact attempt time for connection failures, TLS problems, timeouts, or application errors.
Validate the signature using the provider’s signing secret and the exact raw request body required by that provider. Middleware that parses or changes the body before verification can cause a valid signature to fail. Lemon Squeezy instructs receivers to validate each request against its signing secret; keep that secret out of logs and client-visible code. See Lemon Squeezy’s webhook guide.
Return success only after durable capture
Once the request is validated, persist the event or enqueue it durably, then return the provider’s expected success response promptly. Run slower work—such as provisioning a license, calling another API, or sending email—in a background worker where possible. A success response should mean your system has safely accepted responsibility for processing the event, not merely that the HTTP handler received bytes.
Lemon Squeezy says to return HTTP 200; its guide says other status codes trigger up to three more attempts and recommends storing event data so processing does not depend on another delivery. Paddle’s current documentation says receivers should respond within five seconds and recommends asynchronous processing. These are provider-specific requirements, not universal webhook rules. Check Lemon Squeezy’s guide and Paddle’s webhook delivery documentation for current details.
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Why did I receive the same webhook twice?
Build for repeated delivery. Providers may retry when they do not receive the expected response, and a response can be lost even when your application performed some work. Treat a repeated event as normal input rather than a reason to issue a second license or repeat a non-idempotent action.
- Store the provider’s stable event identifier with a unique database constraint. Use the identifier the actual provider documents—Paddle recommends
event_id—rather than assuming all providers use the same field. - On receipt, validate the signature and persist the event and its processing status before acknowledging it.
- If the same identifier arrives again, recognize it and return success without repeating completed side effects.
- Track in-progress and failed processing separately from completed processing. If a worker crashes after saving an event but before finishing the license change, make that work recoverable instead of silently discarding it as already seen.
Paddle explicitly documents at-least-once webhook delivery and recommends event_id as a deduplication key. Its delivery behavior and identifiers are specific to Paddle; consult Paddle’s documentation for the current contract.
Why is the license status still delayed or unexpectedly reverted?
Delivery order is not necessarily event-creation order. A newer renewal or cancellation update might be applied before an older event arrives; blindly applying the late event can overwrite the current license state.
Paddle states, “We can’t guarantee the order of delivery for webhooks.” It recommends using the event’s occurred_at value when ordering events. For another provider, check its documentation for the relevant timestamp and its meaning rather than assuming the field or behavior is the same.
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- When events conflict or ordering is ambiguous, retrieve the canonical subscription or license state from the provider’s API before changing access.
- Record both receipt time and processing outcome in your own logs so you can distinguish a late delivery from a slow worker.
How to resend a failed webhook and verify recovery
- Fix the cause first. Correct the endpoint, routing, response behavior, signature handling, or processing failure shown by the attempt record.
- Use the provider’s supported replay control. Lemon Squeezy exposes recent webhook requests, payloads, and resend controls in its dashboard. Paddle documents replay for exhausted notifications through its API. Confirm the available controls in the current provider dashboard or API before relying on a replay workflow.
- Inspect the replay attempt. Confirm the destination, response code, and provider-side status show successful delivery.
- Verify application processing. Find the event ID in application logs and confirm it reached a completed state, not just a received or queued state.
- Check the final license state. Confirm the intended access change occurred exactly once and was not overwritten by an older event.
Resending is not a substitute for idempotency: a replay can deliver an event your application partly processed during the original attempt. Lemon Squeezy and Paddle describe different replay mechanisms and retry policies in their own documentation: Lemon Squeezy webhook guide and Paddle webhook delivery documentation.
Provider delivery rules are not interchangeable
Retry limits, acknowledgement deadlines, identifiers, ordering behavior, and replay tools differ by provider and can change. These examples reflect the providers’ documentation as verified on October 3, 2026; consult the linked documentation for current behavior.
Quick Recap
| Provider | Documented delivery details | What to use in troubleshooting |
|---|---|---|
| Lemon Squeezy | Its guide says to return HTTP 200; other codes trigger up to three more attempts. Recent requests can be resent from webhook settings. Lemon Squeezy | Inspect recent requests and payloads; use the dashboard resend control after fixing the endpoint. Its webhook documentation lists event types and test-mode simulation. Event types |
| Paddle | Current documentation says a live account can receive up to 60 retry attempts over 3 days; sandbox behavior differs. It calls for a response within five seconds, documents at-least-once delivery, and does not guarantee order. Paddle | Use the documented event_id for deduplication and occurred_at for ordering; exhausted notifications can be replayed through its API. Verify live versus sandbox policy in current docs. |
| Stripe | The cited support workflow directs operators to inspect failed endpoint attempts and individual attempt status and response details. The cited source does not establish a retry limit or schedule. Stripe | Use endpoint delivery records and response details to diagnose the failure; do not infer retry limits from another provider. |
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