Deployment Frequency: How We Went From Weekly to 20x/Day

The Deploy Fear We deployed once a week. On Thursdays. With a 2-hour deployment window. Three engineers on standby. A rollback plan printed on paper (yes, really). Everyone was terrified of deployments because they were big, risky, and painful. The Paradox: Deploy More = Fail Less Counter-intuitive but proven: increasing deployment frequency reduces failure rate. Weekly deploys: Big changes, high risk, hard to debug Average changeset: 15 PRs, 2000+ lines changed Failure rate: 18% MTTR when fails