Cloudflare Deployment Workflow

Automated deployment workflow with comprehensive pre-flight checks and validation before deploying to Cloudflare Workers.

What This Command Does

1. Validates configuration: Checks wrangler.jsonc/wrangler.toml is properly configured
2. Checks compatibility date: Warns if compatibility_date is old
3. Verifies bindings: Ensures all referenced bindings exist
4. Runs tests: Executes npm test if test script exists
5. Runs build: Executes npm run build if build script exists
6. Confirms deployment: Shows what will be deployed and asks for confirmation
7. Executes deployment: Runs wrangler deploy
8. Verifies success: Checks deployment succeeded
9. Updates memory: Saves deployment details to living memory (if successful)
10. Monitors: Offers to tail logs after deployment

Process

Step 1: Validate Configuration

Read and validate wrangler configuration:

• Locate wrangler.jsonc or wrangler.toml
• Verify required fields (name, main, compatibility_date)
• Check entry point file exists
• Validate binding configurations (KV, D1, R2, etc.)
• Parse environment if --env flag provided

Step 2: Check Compatibility Date

Check compatibility_date:

• If older than 6 months, warn user it's outdated
• Suggest updating to recent date
• Offer to update automatically if user agrees

Step 3: Verify Bindings

For each binding in configuration:

• KV: Check namespace exists (if possible)
• D1: Verify database exists
• R2: Verify bucket exists
• Vectorize: Check index exists

If bindings don't exist, inform user and offer to create them.

Step 4: Check for D1 Migrations

If D1 bindings exist:

• Check if migrations/ directory exists
• List pending migrations: wrangler d1 migrations list DB [--env ENV] [--remote]
• If pending migrations, ask user:
  • "You have pending D1 migrations. Apply them before deploying?"
  • If yes, run: wrangler d1 migrations apply DB [--env ENV] --remote

Step 5: Run Tests (if available)

Check package.json for test script:

• If "test" script exists and is not placeholder ("echo "Error...")
• Run: npm test
• If tests fail, ask user:
  • "Tests failed. Continue with deployment anyway? (not recommended)"
  • If no, abort deployment

Step 6: Run Build (if available)

Check package.json for build script:

• If "build" script exists
• Run: npm run build
• If build fails, abort deployment

Step 7: Dry Run (if --dry-run flag)

If user provided --dry-run flag:

wrangler deploy --dry-run [--env ENV]

Show results and exit (don't deploy).

Step 8: Confirm Deployment

Show user what will be deployed:

Ready to deploy:
- Worker: my-worker
- Environment: production (or default if no --env)
- Entry point: src/index.ts
- Bindings: KV (CACHE), D1 (DB), R2 (UPLOADS)
- Compatibility date: 2024-01-15

Ask for confirmation:

• "Deploy to [environment]? (yes/no)"
• If production/no --env, add extra warning:
  • "⚠️ This will deploy to PRODUCTION. Are you sure?"

Step 9: Execute Deployment

Run wrangler deploy:

wrangler deploy [--env ENV]

Show verbose output so user sees progress.

Step 10: Verify Deployment

Check if deployment succeeded:

• Look for success message in output
• If successful, show deployment URL
• List recent deployments: wrangler deployments list [--env ENV]

Step 11: Update Living Memory

If deployment successful and living memory exists:

• Update .claude/cloudflare-expert.local.md
• Add to "Recent Deployments" section:

  - [YYYY-MM-DD HH:MM] Deployed to [environment]
    - Worker: [name]
    - Version: [if tracked]
    - Bindings: [list]
  

Prompt user: "Would you like me to remember this deployment configuration?"

Step 12: Post-Deployment Options

Offer user next steps:

1. "Monitor logs with wrangler tail [--env ENV]?"
2. "Test the deployment at [URL]?"
3. "View deployment details?"

If user wants logs, run:

wrangler tail [--env ENV]

Common Issues and Solutions

Issue: Authentication required

Solution: Run wrangler login or set CLOUDFLARE_API_TOKEN

Issue: Binding not found

Solution:

• Check binding exists: wrangler kv:namespace list (for KV)
• Verify binding ID matches wrangler.jsonc
• Create missing binding if needed

Issue: Migration not applied

Solution:

wrangler d1 migrations apply DB --env production --remote

Issue: Compatibility date too old

Solution: Update wrangler.jsonc:

{
  "compatibility_date": "2024-01-15"  // Use recent date
}

Issue: Tests failing

Solution:

• Fix tests before deploying
• Or use --dry-run to validate config without deploying
• Or acknowledge risk and proceed (not recommended)

Issue: Deployment failed

Solution:

• Check error message
• Verify all bindings exist
• Ensure migrations applied
• Check authentication
• Validate wrangler.jsonc syntax

Usage Examples

Deploy to production (default):

/cloudflare:deploy

Deploy to staging:

/cloudflare:deploy --env staging

Dry run (validate without deploying):

/cloudflare:deploy --dry-run

Deploy to specific environment with dry run:

/cloudflare:deploy --env production --dry-run

Important Notes

• Always show verbose output for transparency
• Run pre-flight checks even if user is experienced
• Warn loudly when deploying to production
• Offer to apply D1 migrations before deploying
• Run tests if they exist (don't skip silently)
• Update living memory after successful deployment
• Offer post-deployment monitoring

Safety Features

1. Double confirmation for production: Extra prompt for production deploys
2. Test enforcement: Won't deploy if tests fail (unless user overrides)
3. Migration warnings: Alerts about pending migrations
4. Dry run option: Validate without deploying
5. Deployment verification: Confirms deployment succeeded

References

• Use deployment-strategies skill for CI/CD and deployment patterns
• Use wrangler-workflows skill for wrangler commands
• Use cloudflare-platform skill for binding questions

Auto-activate relevant skills as needed during the workflow.