5 Critical Mistakes I Made Deploying Cloudflare Workers to Production (And How to Avoid Them)

I've deployed over 50 Cloudflare Workers to production. And honestly? I've made every mistake
in the book.

Some were minor annoyances. Others were costly. One mistake cost my company an entire morning
of downtime. Another exposed a security vulnerability I didn't catch until a user reported it.

But each mistake taught me something. And after years of learning (the hard way), I finally
have a system that works.

Today, I want to share the mistakes I made—and how you can avoid them.

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Mistake #1: Deploying Without a Security Checklist

What I did:
Built a Worker, tested it locally, and deployed. Seemed fine.

What I missed:

• No CORS configuration (browser blocked requests)
• No rate limiting (got slammed with requests)
• No security headers (exposed to XSS attacks)
• Secrets hardcoded in environment... wait, actually, I was paranoid enough to use Cloudflare Secrets, but I didn't validate input

The consequence:
My API got hit with a flood of requests. No rate limiting = crashed. Then a user reported
they could inject malicious data.

How to avoid it:
Create a security checklist BEFORE deploying:

• ✅ CORS configured for your domain only (not wildcard)
• ✅ Rate limiting enabled
• ✅ Input validation on all endpoints
• ✅ Security headers set (HSTS, CSP, etc.)
• ✅ Secrets in Cloudflare (not code)
• ✅ JWT tokens have expiration
• ✅ Error messages don't leak system info

I now use a checklist for every single deployment. Takes 10 minutes. Saves countless headaches.

This is exactly why I created a 7-checklist system (plus production-ready code templates)
for deploying Workers safely. Security is just one of them. Get the complete guide for $29 →

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Mistake #2: Not Testing Performance Before Production

What I did:
Built locally, tested in staging, deployed to production.

What I missed:
My database queries were slow. My caching wasn't configured. I didn't realize some endpoints
took 2+ seconds to respond.

The consequence:
Users complained about slowness. My CF Workers bill was higher than expected (unnecessary
database calls). I had to rollback and optimize.

How to avoid it:
Before deploying:

• Test response time under load (not just locally)
• Check P95 latency (not just average)
• Profile database queries
• Implement caching for repeated requests
• Verify bundle size is under 1MB

A simple console.time() during development would have caught this immediately.

console.time('db-query');
const users = await env.DB.prepare('SELECT * FROM users').all();
console.timeEnd('db-query');
// Output: db-query: 145ms

I learned this the hard way, which is why I included a complete performance checklist and
a caching template in my deployment guide. Check it out → $29

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Mistake #3: Forgetting to Set Up Proper Logging

What I did:
Deployed, assumed it would work, didn't set up any monitoring.

What I missed:
When something broke, I had no idea what happened. No logs. No error tracking. Just... nothing.

The consequence:
Spent 2 hours debugging blindly. Could have found the issue in 5 minutes with proper logs.

How to avoid it:
Set up logging from day one:

• ✅ Enable Workers Logs in wrangler.toml
• ✅ Structured logging (JSON format)
• ✅ Include RequestID for tracing
• ✅ Log different levels (DEBUG, INFO, WARN, ERROR)
• ✅ Set up alerts for high error rates

Example:

const logger = new Logger({
  requestId: crypto.randomUUID(),
  path: url.pathname,
  method: request.method
});

logger.info('Request received', { endpoint: '/api/users' });
// Output: {"timestamp":"2025-12-25T...", "level":"INFO", "message":"Request received", ...}

I've since built a structured logging template and included it in my guide. Along with
monitoring, health checks, and everything else you need. Get $29 access →

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Mistake #4: Not Having a Rollback Plan

What I did:
Deployed a broken version and panicked when it broke production.

What I missed:
I had no idea how to quickly revert to the previous version. My fix took 30 minutes because
I was scrambling.

The consequence:
30 minutes of downtime for users. Lost trust. Could have been 2 minutes with a practiced
rollback procedure.

How to avoid it:
Before deploying to production:

• Know the rollback command by heart: wrangler rollback DEPLOYMENT_ID
• Test it in staging first
• Document it in your team's runbook
• Practice it (seriously, do a test rollback)

A 5-minute practice session saves 30 minutes of panic later.

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Mistake #5: Not Documenting What You Did

What I did:
Deployed a critical update, didn't document the changes, didn't tell my team.

What I missed:
My coworker deployed an hour later without knowing about my changes. Created a conflict.

The consequence:
Confused config, broken deployment, rolled back my changes, had to redeploy the next day.

How to avoid it:
Create a deployment checklist for your team:

• What changed?
• Why did it change?
• What to watch for?
• How to rollback?
• Who deployed it?
• When?

A 5-minute deployment log saves hours of confusion later.

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The System That Works

After all these mistakes, I finally developed a system:

Before deployment:

1. Use a pre-deployment checklist (configuration, secrets, database)
2. Use a security checklist (auth, CORS, headers, validation)
3. Use a performance checklist (caching, queries, bundle size)
4. Use a testing checklist (unit, integration, staging)

During deployment:

1. Use a deployment-day checklist (health checks, metrics, alerts)
2. Monitor continuously for 24 hours
3. Watch error rate and response time

After deployment:

1. Use a post-deployment checklist (logs, metrics, team notification)
2. Document what changed
3. Celebrate (you earned it)

This system has eliminated 95% of my production issues. Now when things do break, they're
caught immediately and fixed in minutes instead of hours.

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The Boring But Necessary Truth

Deployments aren't glamorous. Checklists aren't exciting. But they work.

The best teams I've worked with weren't the smartest. They were the most disciplined.

They had checklists. They followed them. They rarely had incidents.

And when something did go wrong? They had a plan. Fixed it in minutes. Moved on.

That's why I spent time compiling all of this into one guide. Not to sell you something,
but because I genuinely believe every developer should have this. It includes:

• ✅ 25-page production deployment guide
• ✅ 7 printable checklists (ready to print and tape to your desk)
• ✅ 9 production-ready code templates

For just $29. Get it here →

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Where to Start

If you're reading this and thinking "yeah, I should probably have a system..."

Here's what I recommend:

1. Print a security checklist and tape it to your monitor
2. Create a simple deployment checklist for your team (or grab one from my guide)
3. Set up one alert in Cloudflare for high error rates
4. Test a rollback once

Takes 1 hour. Could save you from a 6-month security nightmare.

Or, if you want everything ready to go, grab the complete guide for $29 →
It has all the templates, checklists, and code examples already done.

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Final Thoughts

I learned these lessons through expensive mistakes. You don't have to.

The smartest move isn't writing perfect code on the first try. It's creating a system that
catches mistakes before they hit production.

Checklists. Monitoring. Logging. Rollback procedures.

Boring? Maybe. But your ops team will love you. Your users won't experience outages. Your
CEO won't yell at you.

Worth it.

Have you made any of these mistakes? What did you learn? Let me know in the comments—I'd
love to hear about your deployment war stories.

And if you're looking for a complete system to avoid these issues, I've put together
everything here for $29 →

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What's Inside the Guide

Since I keep mentioning it, here's what you actually get for $29:

The Guide:

• 25 pages of production deployment knowledge
• Everything from pre-deployment config to post-deployment monitoring
• Real errors and how to solve them

The Code:

• 9 production-ready TypeScript templates
  • JWT Authentication
  • CORS Handler
  • Rate Limiting
  • Caching Strategy
  • Security Headers
  • Structured Logging
  • Input Validation
  • Health Checks
  • Complete Worker Setup

The Checklists:

• 7 printable checklists (one for each phase)
  • Pre-Deployment
  • Security
  • Performance
  • Testing
  • Monitoring
  • Deployment Day
  • Post-Deployment

The Extras:

• Configuration examples
• Complete troubleshooting guide
• FAQ with 20+ answered questions

Everything ready to use, customize, and scale.

Get it for $29 →

30-day money-back guarantee if you're not satisfied.