Deploy Checklist

Generate comprehensive deployment checklists for safe, documented releases.

When to Use This Skill

• •Before deploying a new release to any environment
• •When preparing for production deployments
• •When you need a documented rollback plan
• •For compliance or audit requirements around deployments
• •When onboarding team members to deployment processes

Input

Provide the following:

1. •

   Target

   • •Service or application name
   • •Target environment (staging, production, etc.)
   • •Release version or tag
2. •

   Scope

   • •Commits or PRs included in this release
   • •Features being released
   • •Bug fixes included
3. •

   Strategy Preference (optional)

   • •Rolling update
   • •Blue-green
   • •Canary
   • •Or let the checklist recommend based on risk

Workflow

Step 1: Analyze Changes

Review what's being deployed:

• •List commits since last deployment
• •Identify database migrations
• •Note configuration changes
• •Check dependency updates
• •Flag feature flag changes

Step 2: Assess Risk

Evaluate deployment risk:

• •Breaking changes
• •Migration complexity
• •Rollback difficulty
• •Blast radius

Step 3: Generate Pre-flight Checklist

Create verification items for:

• •Code Readiness - tests pass, reviewed, merged
• •Environment Readiness - resources available, configs updated
• •Observability - dashboards ready, alerts configured
• •Communication - stakeholders notified, runbook available

Step 4: Define Rollout Strategy

Based on risk assessment, recommend:

• •Rollout type (rolling, blue-green, canary)
• •Traffic progression (for canary)
• •Rollout steps with verification gates
• •Timeline estimate

Step 5: Create Verification Checklist

Define what to check after deployment:

• •Immediate (0-5 min) - pods healthy, no errors
• •Short-term (5-30 min) - metrics normal, features working
• •Extended (30 min - 2 hr) - performance stable, no regressions

Step 6: Document Rollback Plan

For every deployment, include:

• •Rollback trigger conditions
• •Rollback commands/steps
• •Rollback verification
• •Communication plan if rollback needed

Output

Produce a deployment checklist following the template in references/deploy-checklist-template.md.

The checklist should include:

• •Summary (service, environment, version, date)
• •Changes included (features, fixes, migrations, dependencies)
• •Pre-flight checklist
• •Deployment strategy with steps
• •Verification checklist by time window
• •Rollback triggers and plan

Investigation Areas

Constraints

• •Checklist only - this skill generates documentation, not executes deployments
• •Always include rollback - every checklist must have a rollback plan
• •Be specific - include actual commands, not just descriptions
• •Risk-appropriate - match strategy complexity to deployment risk

Example

Example: API Service Production Deploy

Input:

• •Service: user-api
• •Environment: production
• •Version: v2.3.0
• •Changes: 3 features, 1 migration, 2 bug fixes

Output Summary:

Deployment: user-api v2.3.0 → production

Risk Assessment: MEDIUM
- Database migration (additive, backward compatible)
- New authentication flow (feature flagged)

Strategy: Canary (10% → 50% → 100%)

Pre-flight:
✓ All tests passing
✓ Migration tested in staging
✓ Feature flag configured (disabled by default)
✓ Dashboards bookmarked
✓ On-call notified

Rollback Triggers:
- Error rate > 1%
- P99 latency > 500ms
- Migration failure

Rollback Command:
kubectl rollout undo deployment/user-api -n production

Begin by analyzing the changes included in this deployment before generating the checklist.