Deployment Automation Enforcer

Deployment Automation Enforcer

ROLLBACK CHECKPOINT (COMPLETE FIRST)

MANDATORY before creating TodoWrite:

• Rollback script exists? [Path: _______ | or "NEW - will create first"]
• Tested in staging? [Date: _______ | or "must test before production"]
• Duration measured? [_____ minutes]
• Triggers defined? [List: _______]

Why first: 27% skip rollback when checkpoint appears later.

---

TodoWrite Requirements

CREATE TodoWrite with 4 sections (19+ items total):

Section order matters: You cannot define failure recovery without observability to detect failures.

---

Verification Checkpoint

After creating TodoWrite, verify 3 random items:

Each item must have ALL THREE:

• ✓ Concrete numbers/​thresholds ("error rate > 5%", "15 min timeout")
• ✓ Specific tools ("GitHub Actions", "CloudWatch", "PagerDuty")
• ✓ Measurable outcome ("rollback tested on [date]", "alert fires within 5min")

---

Section Requirements

Automation (5+ items)

• Identify manual steps in current deployment
• Replace with automated scripts/​workflows (GitHub Actions, GitLab CI)
• Idempotency checks for safe re-runs
• Rollback automation for this change
• Document exceptions for remaining manual steps

Observability (5+ items) - BEFORE Failure Recovery

• Deployment logging (structured: deployment-id, timestamps, steps)
• Failure alerts (PagerDuty/​SNS on failure, error rate spike)
• Metrics (duration, success rate in CloudWatch/​Datadog)
• Health endpoint (/​health returns 200 + dependency status)
• Log/​metric locations documented

Failure Recovery (5+ items) - AFTER Observability

• Failure scenarios defined (won't start, migration fails, health check fails)
• Automated rollback triggers (error rate > X%, failed health checks Y minutes)
• Health checks post-deployment
• Rollback tested in staging (date, duration, success)
• Manual recovery documentation as last resort

Verification (4+ items)

• Pre-deployment tests automated (unit, integration, lint)
• Smoke tests post-deployment (critical flows, key endpoints)
• Monitoring/​alerts verified working (trigger test alert)
• Rollback procedure accessible (script in repo, documented)

---

Red Flags - STOP When You Think:

---

Response Templates

"We'll Add Rollback Later"

❌ BLOCKED: Cannot deploy without rollback capability.

• 27% skip rollback when not required upfront
• 80% of "add later" items never get added
• Manual recovery takes 30+ minutes vs 2 minutes automated
• Production incidents without rollback = extended downtime + customer impact

Required to override:

1. Specific retrofit date (not "later")
2. Budget allocated (engineer-weeks + incident risk cost)
3. Risk acceptance signed by decision maker
4. Interim mitigation plan (24/​7 on-call? manual monitoring?)

---

Override Requirements

To skip ANY requirement, provide ALL 4:

1. Specific retrofit date (not "later")
2. Budget allocated (engineer-weeks + incident risk)
3. Risk acceptance signed by decision maker
4. Interim mitigation plan (24/​7 on-call? manual monitoring?)

---

Self-Grading Before Complete

[ ] 19+ items across 4 sections
[ ] 80%+ items have concrete numbers
[ ] 80%+ items name specific tools
[ ] 100% items have measurable outcomes
[ ] 3 random items pass specificity test
[ ] Rollback checkpoint completed
[ ] Observability BEFORE Failure Recovery (correct order)

Grade 7+/​8: Ready to proceed
Grade <7: Revise TodoWrite

---

Evidence Collection

Before marking complete:

• Automation code link (workflow file URL)
• Staging deployment log (screenshot/​excerpt)
• Monitoring dashboard screenshot
• Rollback test evidence (log with timestamp, duration)
• Alert test confirmation