Definitely Stripe should have done a better job here. However, also points to the risk of allowing service providers to handle your security. Maybe there should have been a back test and or a "maker" "checker" control for pushing new security rules.
Putting the webhook callback behind CloudFlare was the mistake IMO.
And Cloudflare is well known for randomly throwing up "Checking your browser before accessing example.com" interstitials and captchas and suchlike - of course you don't want bot detection on your callback API.
[1] https://stripe.com/docs/ips?locale=en-GB#webhook-notificatio...