Why uptime checks pass while checkout or Stripe webhooks break

We load one page you pick and check the status code and an expected title or phrase. One miss is not an alert. You get an email after 2 failures in a row, and another when it passes again.

With a read-only restricted key, we look for webhook events Stripe still hasn't delivered after about 15 minutes, endpoints that are disabled, and sales that go quiet for about 48 hours when the previous 14 days say they should still be coming in.

Free: 1 site, checked once a day. Pro: $19 a month, up to 3 sites checked hourly. You prove you own the site before any check runs. Compare plans

A basic monitor requests a URL and reads the answer. UptimeRobot's free plan, for example, lists HTTP checks and a keyword monitor that looks for a word in the page's HTML. UptimeRobot: pricing A home page that loads says nothing about the code that runs after someone pays.

Your monitor calls your site. Stripe calls your webhook route. If that route answers with an error or a redirect, Stripe counts a failed delivery. Stripe treats any 3xx as a failure too. Stripe: fix HTTP status codes Your pages still load, so the monitor stays green.

In live mode Stripe retries a failed event for up to three days with exponential backoff. In a sandbox it retries three times over a few hours. Stripe: automatic retries Payments can go through in Stripe while your app never hears about them, and nothing looks down.

Every webhook endpoint has a status of enabled or disabled. Stripe API: Webhook Endpoint object A disabled endpoint, or a live site with only a sandbox endpoint, gets no events. No page goes down.

A page check doesn't press Pay. Wrong keys, a broken redirect after payment, or a missing price can all fail behind a page that loads. To test the flow itself, use a check that clicks through it. Checkly lists browser checks with Playwright for flows like logins and checkouts. Checkly: pricing Pingdom lists transaction monitoring for flows like a shopping cart checkout. Pingdom Better Stack lists Playwright transaction monitoring. Better Stack: uptime

A plain uptime monitor. UptimeRobot, Better Stack, Pingdom and Checkly all offer one. Better Stack's page says its free tier has 10 monitors with 3-minute checks. Better Stack: uptime

A browser or transaction check that clicks through your flow, as above. Use a test mode or a test product so a check never makes a real charge.

Open your endpoint in Stripe and read the Event deliveries tab. Stripe: webhooks To find what you missed, list events with delivery_success=false. It covers the last 30 days. Stripe: process undelivered events If you route webhooks through a gateway such as Hookdeck, it has its own delivery view. Its pricing page lists a free Developer plan for up to 10,000 events. Hookdeck: pricing

If successful charges stop on a day they normally come in, check your checkout and your webhook deliveries. Compare recent charges with a normal day for your app.