I've worked at one of the top fintech firms, whenever we do a config change or deployment, we are supposed to have rollback plan ready and monitor key dashboards for 15-30 minutes.
The dashboards need to be prepared beforehand on systems and key business metrics that would be affected by the deployment and reviewed by teammates.
I've never seen a downtime longer than 1 minute while I was there, because you get a spike on the dashboard immediately when something goes wrong.
For the entire system to be down for 10+ minutes due to a bad config change or deployment is just beyond me.
Comparing the difficulty of running the world’s internet traffic with hundreds of customer products with your fintech experience is like saying “I can lift 10 pounds. I don’t know why these guys are struggling to lift 500 pounds”.
If there’s indeed a 5 min lag in monitoring dashboard in Cloudflare, I honestly think that's a pretty big concern.
For example, a simple curl script on your top 100 customers' homepage that runs every 30 seconds would have given the warning and notifications within a minute. If you stagger deployments at 5 minute intervals, you could have identified the issue and initiated the rollback within 2 minutes and completed it within 3 minutes.