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Cloudfare outage post mortem
(blog.cloudflare.com)
This is a most excellent place for technology news and articles.
There are technical solutions to this. You update half your servers, and then if they die you just disconnect them from the network while you fix them and then have your own unaffected servers take up the load. Now yes, this doesn't get a fixout quickly, but if you update kills your entire system, you're not going to get the fix out quickly anyway.