Deployment Checklist Maker

Generates an operational deployment runbook from actual project configuration. Includes pre-flight checks, atomic deploy steps, health verifications, and an explicit rollback procedure.

1. Purpose

Prevent deployment outages and failed releases. A "Deployment Checklist" is a sequential runbook ensuring migrations, environment variables, dependencies, and rollbacks are verified before touching production.

2. When to Use

Use this skill when:

• Planning a production or staging release.
• Verifying database migrations and environment variable changes.
• User requests: "Create a deployment checklist for this release."

3. When Not to Use

• Do not use to draft feature release notes for users; use release-notes-drafter.
• Do not use to plan local file cleanups; use reversible-cleanup-planner.

4. Required Inputs

• project_type: Framework/runtime (e.g. Next.js, FastAPI, Go).
• deployment_target: Platform (e.g. AWS ECS, Vercel, Kubernetes, Docker).
• database_changes: Are migrations included? (Yes / No).

5. Missing-Input Behavior

1. If deployment_target is unknown: inspect repository for Dockerfile, k8s/, docker-compose.yml, or CI/CD workflow files (.github/workflows/).
2. Always mandate an explicit Rollback Procedure. Never emit a checklist without rollback steps.
3. If database migrations exist: place migration verification before traffic routing.

6. Procedure

Follow these numbered actions:

1. Action 1: Pre-Deployment Verification (Pre-Flight)
   • All tests green on main branch.
   • Clean working tree, tagged release commit.
   • Environment variables configured in target environment.
2. Action 2: Deployment Actions
   • Run database migrations (with backward-compatible columns).
   • Deploy build artifact or container image.
3. Action 3: Post-Deployment Smoke Test
   • Check /healthz or status endpoint.
   • Check error rate metrics for 5 minutes.
4. Action 4: Rollback Trigger & Procedure
   • State exact command to revert artifact and rollback database.
5. Action 5: Emit Checklist
   • Format per Section 8.

7. Decision Rules

• If database migrations drop columns: flag as High Risk and mandate a 2-phase migration (deprecate first, drop in next release).
• If healthcheck endpoint fails post-deploy: immediately initiate Rollback Procedure.

8. Output Format

Emit the checklist using this template:

### Deployment Checklist: [Service Name] -> [Target Environment]

- **Target**: [e.g., Kubernetes Production / us-east-1]
- **Risk Level**: [Low | Medium | High]
- **Estimated Downtime**: [Zero-downtime | N minutes maintenance]

#### 1. Pre-Flight Checks
- [ ] CI pipeline is green on commit `[hash]`.
- [ ] Required environment variables verified in target environment.
- [ ] Database backup snapshot created.

#### 2. Deployment Steps
1. `[Step 1 command or action]`
2. `[Step 2 command or action]`

#### 3. Post-Deployment Verification
- [ ] Healthcheck endpoint `[URL]` returns HTTP 200.
- [ ] Error rate metrics remain below baseline threshold (< 0.1%).

#### 4. Rollback Procedure
If verification fails, execute immediately:
```bash
[Rollback command]

## 9. Verification Checklist
- [ ] Checklist includes Pre-Flight, Deployment, Post-Deploy, and Rollback.
- [ ] Rollback procedure is explicit and actionable.
- [ ] Database migration risks are explicitly flagged.
- [ ] Healthcheck URL or command is concrete.

## 10. Common Failures and Recovery
| Failure Symptom | Cause | Recovery Action |
| :--- | :--- | :--- |
| Missing rollback plan | Assuming deploy will succeed | Add rollback command before marking checklist complete. |
| Incompatible DB migration | Breaking old code during rollouts | Mandate expand-contract migration pattern. |

## 11. Stop or Escalation Conditions
Stop and ask the user when:
- Deployment involves irreversible data destruction without backup capability.

## 12. Examples

### Example 1: Successful Execution
**Input:**
```text
Service: payments-api
Target: Docker Compose on Ubuntu VM
DB: PostgreSQL migration adding index

Output:

### Deployment Checklist: payments-api -> Production

- **Target**: Docker Compose on Ubuntu VM
- **Risk Level**: Low (Zero-downtime index creation)
- **Estimated Downtime**: Zero-downtime

#### 1. Pre-Flight Checks
- [ ] All unit and integration tests green on `main`.
- [ ] PostgreSQL snapshot created before running index migration.
- [ ] Confirmed `.env` contains valid `STRIPE_KEY` on production VM.

#### 2. Deployment Steps
1. SSH to production server: `ssh deploy@payments-prod.internal`.
2. Pull latest container image: `docker compose pull api`.
3. Run database migrations: `docker compose run --rm api npm run db:migrate`.
4. Restart service: `docker compose up -d --no-deps api`.

#### 3. Post-Deployment Verification
- [ ] Check container health: `docker compose ps` shows `healthy`.
- [ ] Verify endpoint: `curl -I https://payments.example.com/healthz` returns HTTP 200.

#### 4. Rollback Procedure
If health check fails:
```bash
docker compose up -d --no-deps api:previous-tag

### Example 2: Ambiguous or Missing Input
**Input:**
```text
Deploy app.

Output:

### Deployment Checklist: Halted - Missing Configuration

- **Status**: Halted

Please provide:
1. The service name or repository.
2. The deployment platform (e.g. AWS ECS, Kubernetes, Vercel, Docker).
3. Whether database migrations or schema updates are involved.

Example 3: Expected Final Output

Output:

### Deployment Checklist: frontend-web -> Vercel Production

- **Target**: Vercel Production
- **Risk Level**: Low
- **Estimated Downtime**: Zero-downtime

#### 1. Pre-Flight Checks
- [ ] `npm run build` succeeds locally without warnings.
- [ ] Preview deployment verified on staging domain.

#### 2. Deployment Steps
1. Promote preview to production via Vercel CLI or GitHub release tag.

#### 3. Post-Deployment Verification
- [ ] Visit home page and verify login modal loads.

#### 4. Rollback Procedure
- Instant rollback in Vercel dashboard to previous deployment ID.