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skills/deployment-cloudflare/checklists/deployment-checklist.md

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+# Deployment Checklist
+
+**Use before deploying to production.**
+
+## Pre-Deployment
+
+### Doppler Configuration
+- [ ] All required secrets set in Doppler production environment
+- [ ] DOPPLER_TOKEN added to GitHub repository secrets
+- [ ] CLOUDFLARE_API_TOKEN added to GitHub repository secrets
+- [ ] Test Doppler access: `doppler secrets --config production`
+
+### Wrangler Configuration
+- [ ] wrangler.production.toml configured with correct routes
+- [ ] KV namespaces created and IDs added to wrangler.toml
+- [ ] R2 buckets created and names added to wrangler.toml
+- [ ] Custom domain DNS configured in Cloudflare
+- [ ] Connection pool settings match database capacity
+
+### Database
+- [ ] Migrations tested locally
+- [ ] Migration reversible (has downgrade)
+- [ ] Seed data prepared for production (if needed)
+- [ ] DATABASE_URL_ADMIN has elevated permissions for migrations
+- [ ] Connection pooling configured (PlanetScale)
+
+### Application
+- [ ] All tests passing locally
+- [ ] All tests passing in CI
+- [ ] Build completes without errors
+- [ ] No TypeScript errors
+- [ ] No console.log statements in production code
+- [ ] Environment variables validated
+
+### GitHub Actions
+- [ ] Workflow file present (.github/workflows/deploy-production.yml)
+- [ ] Workflow triggers configured (push to main)
+- [ ] Node.js version matches local (22)
+- [ ] Doppler CLI action configured
+- [ ] Smoke tests configured
+
+## During Deployment
+
+### Deployment Steps
+- [ ] Merge PR to main branch
+- [ ] GitHub Actions workflow triggered
+- [ ] Tests pass in CI
+- [ ] Build completes successfully
+- [ ] Database migrations run successfully
+- [ ] Workers deployment completes
+- [ ] Secrets injected into Workers
+- [ ] Smoke tests pass
+
+### Monitoring
+- [ ] Watch deployment logs in GitHub Actions
+- [ ] Monitor Cloudflare Workers dashboard
+- [ ] Check Wrangler tail for errors
+- [ ] Verify no Sentry errors
+- [ ] Verify application loads at production URL
+
+## Post-Deployment
+
+### Validation
+- [ ] Production URL loads successfully
+- [ ] Authentication works (login/logout)
+- [ ] Database queries work (tenant isolation)
+- [ ] File uploads work (R2 storage)
+- [ ] Session management works (KV storage)
+- [ ] API endpoints respond correctly
+
+### Smoke Tests
+- [ ] Critical user flows tested
+- [ ] Multi-tenant isolation verified
+- [ ] Performance acceptable (< 500ms response time)
+- [ ] No console errors in browser
+- [ ] Mobile responsive (if applicable)
+
+### Rollback Readiness
+- [ ] Know how to rollback Workers: `npx wrangler rollback`
+- [ ] Know how to rollback database: `drizzle-kit migrate:rollback`
+- [ ] Emergency contacts notified
+- [ ] Linear issue updated with deployment status
+
+## Rollback Triggers
+
+Rollback immediately if:
+- [ ] Smoke tests fail
+- [ ] Critical user flow broken
+- [ ] 500 errors in production
+- [ ] Database connection failures
+- [ ] Authentication broken
+- [ ] Multi-tenant isolation breach
+
+## Post-Deployment Documentation
+
+- [ ] Update Linear issue with deployment notes
+- [ ] Document any manual steps taken
+- [ ] Update team on deployment status
+- [ ] Schedule postmortem if issues occurred
+- [ ] Update runbook with any new learnings