cloudthinker-ai Deployment Checklist Skill
Run a thorough pre- and post-deployment safety check for {{ service_name }} {{ version }} to {{ environment }}.
Workflow
Step 1 — Gather Deployment Context
Collect the following information to complete the checklist:
- Code changes: Fetch the PR/MR or compare tag diff to understand scope of changes
- Changelog / Release notes: Review what is in this release
- Test status: Confirm all CI checks pass for the target commit/tag
- Migration status: Check if any database or infrastructure migrations are included
- Dependency changes: Review
package.json,requirements.txt,go.mod, etc. for dependency updates - Feature flags: List any feature flags introduced or changed in this release
Step 2 — Pre-Deployment Checklist
Go through each item. Mark PASS, FAIL, or SKIP with reasoning:
PRE-DEPLOYMENT CHECKLIST
Service: {{ service_name }}
Version: {{ version }}
Environment: {{ environment }}
Rollback: {{ rollback_version | "Not specified" }}
Date: [auto-populated]
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
READINESS GATES
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
[ ] All CI tests passing on target commit
[ ] Code review approved (≥2 reviewers for production)
[ ] Security scan / SAST passed
[ ] No known CVEs introduced in dependencies
[ ] QA/staging validation complete
MIGRATIONS & DATA
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
[ ] No database migrations — OR — migrations reviewed and tested
[ ] Migrations are backwards-compatible (old code can run against new schema)
[ ] Migration rollback procedure documented
[ ] Data backups confirmed for {{ environment }}
INFRASTRUCTURE & CONFIG
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
[ ] Environment variables / secrets updated for {{ environment }}
[ ] Infrastructure changes (Terraform/CDK) applied or not needed
[ ] New dependencies/services provisioned
[ ] Load balancer health check paths verified
DEPLOYMENT STRATEGY
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
[ ] Deployment strategy defined: [ ] rolling [ ] blue-green [ ] canary [ ] full-replace
[ ] Rollback procedure documented and tested
[ ] Rollback version confirmed: {{ rollback_version | "❌ NOT SPECIFIED" }}
[ ] On-call engineer notified / on standby
FEATURE FLAGS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
[ ] New feature flags are OFF by default for {{ environment }}
[ ] Existing flag changes reviewed and approved
[ ] Kill switches available for risky features
COMMUNICATIONS
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
[ ] Stakeholders notified (if user-impacting)
[ ] Status page updated (if applicable)
[ ] Customer support briefed (if applicable)
Step 3 — Go / No-Go Decision
Evaluate the checklist results:
- GO: All gates PASS or SKIP with documented justification
- NO-GO: Any FAIL without explicit waiver — block deployment and resolve the failing item
- CONDITIONAL GO: ≥1 SKIP with documented risk accepted by engineering lead
Report the go/no-go decision clearly with reasoning.
Step 4 — Deployment Execution
If GO:
- Trigger deployment via CI/CD pipeline or documented runbook
- Monitor key metrics for 15 minutes post-deploy:
- Error rate (should stay within ±2% of baseline)
- P95 latency (should not increase >20% from baseline)
- CPU/memory on new pods/instances
- Verify health check endpoints return 200
Step 5 — Post-Deployment Checklist
After deployment completes:
POST-DEPLOYMENT CHECKLIST
━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━
[ ] All instances/pods running target version {{ version }}
[ ] Health checks passing on all nodes
[ ] No spike in error rate vs pre-deploy baseline
[ ] No degradation in P95 latency
[ ] Key user journeys validated (smoke test)
[ ] Logs show no unexpected errors
[ ] Monitoring alerts not firing
[ ] Database connections stable
[ ] Feature flags toggled as planned
[ ] Deployment record logged (version, timestamp, deployer)
Step 6 — Stabilization Window
- Monitor for 30 minutes post-deploy before considering deployment complete
- If any POST-DEPLOY item FAILS during this window → initiate rollback
- Rollback trigger:
ERROR RATE > 5%orP95 LATENCY 2x baselinesustained for 5 minutes
Rollback Procedure (if needed)
ROLLBACK INITIATED
Reason: [describe trigger]
Rollback to: {{ rollback_version }}
Steps:
1. Trigger rollback deployment (revert to {{ rollback_version }})
2. Verify old version running on all nodes
3. Confirm metrics return to pre-deploy baseline
4. Notify stakeholders of rollback
5. Create post-mortem issue to investigate root cause
Counter-Rationalizations
| Shortcut | Counter | Why |
|---|---|---|
| "We can skip some steps for this case" | Adapt the workflow steps, don't skip them | Skipped steps are where incidents and oversights originate |
| "The user seems to already know what to do" | Complete all workflow phases with the user | The workflow catches blind spots that experience alone misses |
| "This is a minor case, full process is overkill" | Scale the process down, don't turn it off | Minor cases become major when unstructured; the process scales, not disappears |
| "I'll fill in the details later" | Complete each section before moving on | Deferred details are forgotten; real-time capture is more accurate |
| "The template output isn't necessary" | Always produce the structured output format | Structured output enables comparison, audit trails, and handoff to other teams |
Output Format
Produce a structured checklist report with:
- Summary header (service, version, environment, timestamp, deployer)
- Pre-deployment checklist with PASS/FAIL/SKIP per item
- Go/No-Go decision with justification
- Post-deployment results (after monitoring window)
- Action items (any follow-ups needed)