#rollouts
grep -l "rollouts" /portfolio/* · 3 entriesA generated config file that doubled in size
What I took from Cloudflare's November 2025 outage: a permissions change made a generated file double in size, and the proxy crashed on a limit nobody expected to hit.
1 min readA bad content update, everywhere, at once
What I took from the July 2024 CrowdStrike outage: a configuration update, not a code release, crashed millions of Windows machines because it went to all of them at once.
One bad rule, deployed everywhere at once
What I took from Cloudflare's July 2019 outage: a single regular expression, pushed globally in one go, and why config changes need the same staged rollout as code.