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If 96% of your Stripe webhook deliveries are failing, start with the individual delivery attempts—not the percentage. In Stripe Dashboard, open Webhooks, select the affected endpoint, choose Failed, then open an event and expand its attempt. The HTTP status and response show whether to investigate a timeout, a connection problem, or an HTTP or TLS error. Stripe does not publish 96% as a general webhook failure rate; that figure needs to be verified against the incident’s own logs or Dashboard history.
First, verify what “96% failing” means
Treat 96% as an incident-specific observation, not a Stripe-wide statistic. Before drawing conclusions, establish the numerator (failed attempts or events), the denominator (all attempts or events counted), the time window, the endpoint, and whether the endpoint was receiving live-mode or test-mode events. Retries can create multiple attempts for one event, so counting attempts is not the same as counting unique events.
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Stripe’s troubleshooting guidance recommends investigating the actual failed attempts. The rate alone cannot identify a cause, and different failure conditions may occur at the same endpoint.
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Inspect a failed delivery in Stripe Dashboard
- Open Webhooks in the Stripe Dashboard and select the endpoint showing failures.
- Choose the Failed tab and open an event.
- Expand the webhook attempt and record its HTTP status and response. Check multiple attempts if the endpoint has more than one failure pattern.
Use the observed result to choose the next diagnostic path. A timeout, a connection-denied error, a server-returned HTTP error, and a TLS problem are distinct conditions; do not assume they share one fix. Stripe’s webhook troubleshooting guide links to guidance for the different failure types.
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If the attempt timed out, acknowledge first and process later
A timeout means Stripe established a connection, but the server took too long to respond. Stripe expects a prompt HTTP 2xx response to confirm that the event was received. A handler that waits for slow business logic before responding can miss that expectation; acknowledge receipt promptly, then hand lengthy work to an internal queue or another asynchronous process.
Stripe’s guidance also recommends checking server health and logs. Look for CPU or memory pressure, storage-capacity problems, and application errors around the time of the attempt. A 2xx acknowledgement should mean the event was accepted for handling, not that every downstream task has already completed.
If Stripe could not connect, check reachability
A connection-denied error points to whether Stripe can reach the configured endpoint. Check these in order:
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1Fix the driver behind crashes, sound loss and screen glitches2Clear out junk files and repair common Windows errors3Scan for outdated or missing drivers - takes under a minute- Confirm the endpoint URL is correct, including its hostname and path.
- Check that the hostname resolves to the address you expect.
- Verify that the endpoint is publicly reachable from outside your network.
- Review firewall and network rules for blocks affecting Stripe’s published webhook IP addresses.
Stripe’s connection-denied troubleshooting guide focuses on these URL, DNS, reachability, and network-access checks.
Independent reader supportYour contribution helps us test, update, and keep practical guides available for everyone.Use the response to distinguish other failures
If the attempt reached your server but returned an error, use the actual status and response to investigate that branch rather than treating it as a connectivity issue. Stripe’s troubleshooting material separates 3xx redirects, 4xx and 5xx responses, TLS errors, timeouts, and connection-denied errors. The response is evidence about what happened on that attempt; it does not, by itself, establish why the application produced it.
After the fix, check retries and endpoint status
Stripe automatically retries unsuccessful deliveries using a backoff mechanism. Retries can help deliver an event after a temporary problem, but they do not repair an unhealthy endpoint. After deploying a fix, review subsequent attempts and confirm that the endpoint is acknowledging events successfully.
Stripe says that continued unresponsiveness or errors over several days can result in delivery stopping and the endpoint being disabled. If that happens, check the endpoint’s status and use Stripe’s retry and endpoint guidance to determine what action is needed.
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