Cloudflare BYOIP Prefix Mass Deletion Outage
On February 20, 2026, Cloudflare experienced a critical outage due to a buggy automated cleanup task, affecting 50,000 customers globally.
Step into real CTO scenarios. Make decisions, see how others chose, and discover what actually happened.
Meridian (fictional Series C B2B SaaS)
It's 2:14 PM on a Tuesday. Error rates just spiked from 0.2% to 34%. Three enterprise customers are on the phone with your CEO. You have 60 seconds before someone expects an answer.
FinScale (fictional Series B fintech)
You're the incoming CTO of FinScale, a Series B fintech processing $2M in daily transactions. The monolith is cracking under 10x growth pressure. You have a weekend to choose a strategy.
Veloxa (fictional Series A SaaS startup)
Veloxa just closed a $15M Series A. The lead investor's condition: triple the engineering team from 8 to 24 in six months. Navigate the hiring pace, org structure, and management layer decisions that will define your culture.
TechScale Inc. (fictional)
You're the new CTO of a mid-stage startup with a 500K-line monolith. Revenue is growing 3x YoY, but deployments take 4 hours and the on-call team is burning out. It's time to make some hard decisions.
Real-world CTO challenges and solutions from scaling startups to managing enterprise engineering teams.
RSS FeedHave experience to share? We welcome contributions from technical leaders.
Learn how to contribute