The archive
Issue #003
Production Horror Stories 8 min read· 1 Jun 2026

The Friday Night Deployment

A junior dev. A production deploy. A Friday night. And a CTO who's 30,000 feet in the air. The story of how I debugged a broken deployment from an airplane aisle.

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CTO takeaway

The lesson, minus the scar tissue.

  • Ban Friday deployments. Write it in the company handbook. Enforce it with fire.
  • Build an on-call rotation. One person should always be awake and available.
  • When a junior dev breaks something, it's a reflection on your onboarding and processes, not their skill.
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