---

name: grey-haven-deployment-cloudflare description: Deploy TanStack Start applications to Cloudflare Workers/Pages with GitHub Actions, Doppler, Wrangler, database migrations, and rollback procedures. Use when deploying Grey Haven applications.

v2.0.43: Skills to auto-load for deployment work

skills:

• grey-haven-code-style
• grey-haven-observability-monitoring

v2.0.74: Tools for deployment work

allowed-tools:

• Read
• Write
• MultiEdit
• Bash
• Grep
• Glob
• TodoWrite

---

Grey Haven Cloudflare Deployment

Deploy TanStack Start applications to Cloudflare Workers using GitHub Actions, Doppler for secrets, and Wrangler CLI.

Deployment Architecture

TanStack Start on Cloudflare Workers

• SSR: Server-side rendering with TanStack Start server functions
• Edge Runtime: Global deployment on Cloudflare's edge network
• Database: PostgreSQL (PlanetScale) with connection pooling
• Cache: Cloudflare KV for sessions, R2 for file uploads
• Secrets: Managed via Doppler, injected in GitHub Actions

Core Infrastructure

• Workers: Edge compute (TanStack Start)
• KV Storage: Session management
• R2 Storage: File uploads and assets
• D1 Database: Edge data (optional)
• Queues: Background jobs (optional)

Wrangler Configuration

Basic wrangler.toml

Copyname = "grey-haven-app"
main = "dist/server/index.js"
compatibility_date = "2025-01-15"
node_compat = true

[vars]
ENVIRONMENT = "production"
DATABASE_POOL_MIN = "2"
DATABASE_POOL_MAX = "10"

# KV namespace for session storage
[[kv_namespaces]]
binding = "SESSIONS"
id = "your-kv-namespace-id"
preview_id = "your-preview-kv-namespace-id"

# R2 bucket for file uploads
[[r2_buckets]]
binding = "UPLOADS"
bucket_name = "grey-haven-uploads"
preview_bucket_name = "grey-haven-uploads-preview"

# Routes
routes = [
  { pattern = "app.greyhaven.studio", zone_name = "greyhaven.studio" }
]

Environment-Specific Configs

• Development: wrangler.toml with ENVIRONMENT = "development"
• Staging: wrangler.staging.toml with staging routes
• Production: wrangler.production.toml with production routes

Doppler Integration

Required GitHub Secrets

• DOPPLER_TOKEN: Doppler service token for CI/CD
• CLOUDFLARE_API_TOKEN: Wrangler deployment token

Required Doppler Secrets (Production)

Copy# Application
BETTER_AUTH_SECRET=<random-secret>
BETTER_AUTH_URL=https://app.greyhaven.studio
JWT_SECRET_KEY=<random-secret>

# Database (PlanetScale)
DATABASE_URL=postgresql://user:pass@host/db
DATABASE_URL_ADMIN=postgresql://admin:pass@host/db

# Redis (Upstash)
REDIS_URL=redis://user:pass@host:port

# Email (Resend)
RESEND_API_KEY=re_...

# OAuth Providers
GOOGLE_CLIENT_ID=...
GOOGLE_CLIENT_SECRET=...
GITHUB_CLIENT_ID=...
GITHUB_CLIENT_SECRET=...

# Cloudflare
CLOUDFLARE_ACCOUNT_ID=...
CLOUDFLARE_API_TOKEN=...

# Monitoring (optional)
SENTRY_DSN=https://...@sentry.io/...
AXIOM_TOKEN=xaat-...

GitHub Actions Deployment

Production Deployment Flow

Copy# .github/workflows/deploy-production.yml
- Checkout code
- Setup Node.js 22 with cache
- Install dependencies (npm ci)
- Install Doppler CLI
- Run tests (doppler run --config test)
- Build (doppler run --config production)
- Run database migrations
- Deploy to Cloudflare Workers
- Inject secrets from Doppler
- Run smoke tests
- Rollback on failure

Key Deployment Commands

Copy# Build with Doppler secrets
doppler run --config production -- npm run build

# Run migrations before deployment
doppler run --config production -- npm run db:migrate

# Deploy to Cloudflare
npx wrangler deploy --config wrangler.production.toml

# Inject secrets into Workers
doppler secrets download --config production --format json > secrets.json
cat secrets.json | jq -r 'to_entries | .[] | "\(.key)=\(.value)"' | while read -r line; do
  key=$(echo "$line" | cut -d= -f1)
  value=$(echo "$line" | cut -d= -f2-)
  echo "$value" | npx wrangler secret put "$key"
done
rm secrets.json

Database Migrations

Drizzle Migrations (TanStack Start)

Copy// scripts/migrate.ts
import { drizzle } from "drizzle-orm/node-postgres";
import { migrate } from "drizzle-orm/node-postgres/migrator";
import { Pool } from "pg";

const pool = new Pool({
  connectionString: process.env.DATABASE_URL_ADMIN,
});

const db = drizzle(pool);

async function main() {
  console.log("Running migrations...");
  await migrate(db, { migrationsFolder: "./drizzle/migrations" });
  console.log("Migrations complete!");
  await pool.end();
}

main().catch((err) => {
  console.error("Migration failed:", err);
  process.exit(1);
});

package.json scripts:

Copy{
  "scripts": {
    "db:migrate": "tsx scripts/migrate.ts",
    "db:migrate:production": "doppler run --config production -- tsx scripts/migrate.ts"
  }
}

Rollback Procedures

Wrangler Rollback

Copy# List recent deployments
npx wrangler deployments list --config wrangler.production.toml

# Rollback to previous deployment
npx wrangler rollback --config wrangler.production.toml

# Rollback to specific deployment ID
npx wrangler rollback --deployment-id abc123 --config wrangler.production.toml

Database Rollback

Copy# Drizzle - rollback last migration
doppler run --config production -- drizzle-kit migrate:rollback

# Alembic - rollback one migration
doppler run --config production -- alembic downgrade -1

Emergency Rollback Playbook

1. Identify issue: Check Cloudflare Workers logs, Sentry
2. Rollback Workers: npx wrangler rollback
3. Rollback database (if needed): drizzle-kit migrate:rollback
4. Verify rollback: Run smoke tests
5. Notify team: Update Linear issue
6. Root cause analysis: Create postmortem

Cloudflare Resources Setup

KV Namespace (Session Storage)

Copy# Create KV namespace
npx wrangler kv:namespace create "SESSIONS" --config wrangler.production.toml
npx wrangler kv:namespace create "SESSIONS" --preview --config wrangler.production.toml

# List KV namespaces
npx wrangler kv:namespace list

R2 Bucket (File Uploads)

Copy# Create R2 bucket
npx wrangler r2 bucket create grey-haven-uploads
npx wrangler r2 bucket create grey-haven-uploads-preview

# List R2 buckets
npx wrangler r2 bucket list

Monitoring

Wrangler Tail (Real-time Logs)

Copy# Stream production logs
npx wrangler tail --config wrangler.production.toml

# Filter by status code
npx wrangler tail --status error --config wrangler.production.toml

Sentry Integration (Error Tracking)

Copyimport * as Sentry from "@sentry/browser";

Sentry.init({
  dsn: process.env.SENTRY_DSN,
  environment: process.env.ENVIRONMENT,
  tracesSampleRate: 1.0,
});

Local Development

Wrangler Dev (Local Workers)

Copy# Run Workers locally with Doppler
doppler run --config dev -- npx wrangler dev

# Run with remote mode (uses production KV/R2)
doppler run --config dev -- npx wrangler dev --remote

Supporting Documentation

All supporting files are under 500 lines per Anthropic best practices:

• examples/ - Complete deployment examples

  • github-actions-workflow.md - Full CI/CD workflows
  • wrangler-config.md - Complete wrangler.toml examples
  • doppler-secrets.md - Secret management patterns
  • migrations.md - Database migration examples
  • INDEX.md - Examples navigation

• reference/ - Deployment references

  • rollback-procedures.md - Rollback strategies
  • monitoring.md - Monitoring and alerting
  • troubleshooting.md - Common issues and fixes
  • INDEX.md - Reference navigation

• templates/ - Copy-paste ready templates

  • wrangler.toml - Basic wrangler config
  • deploy-production.yml - GitHub Actions workflow

• checklists/ - Deployment checklists

  • deployment-checklist.md - Pre-deployment validation

When to Apply This Skill

Use this skill when:

• Deploying TanStack Start to Cloudflare Workers
• Setting up CI/CD with GitHub Actions
• Configuring Doppler multi-environment secrets
• Running database migrations in production
• Rolling back failed deployments
• Setting up KV namespaces or R2 buckets
• Troubleshooting deployment failures
• Configuring monitoring and alerting

Template Reference

These patterns are from Grey Haven's production templates:

• cvi-template: TanStack Start + Cloudflare Workers
• cvi-backend-template: FastAPI + Python Workers

Critical Reminders

1. Doppler for ALL secrets: Never commit secrets to git
2. Migrations BEFORE deployment: Run db:migrate before wrangler deploy
3. Smoke tests AFTER deployment: Validate production after deploy
4. Automated rollback: GitHub Actions rolls back on failure
5. Connection pooling: Match wrangler.toml pool settings with database
6. Environment-specific configs: Separate wrangler files per environment
7. KV/R2 bindings: Configure in wrangler.toml, create with CLI
8. Custom domains: Use Cloudflare Proxy for DDoS protection
9. Monitoring: Set up Sentry + Axiom + Wrangler tail
10. Emergency playbook: Know how to rollback both Workers and database