PKI Mistakes That Will Ruin Your Weekend
The certificate failures nobody warns you about
Every PKI disaster follows the same pattern: reasonable decisions made by reasonable people that seem fine until they're not. Usually at 2am. Usually on a holiday weekend. The person who set it up is gone. The documentation doesn't exist. And now it's your problem.
This guide covers the mistakes I've seen repeated across enterprise environments. Not theoretical risks - actual failures that took down production and triggered security incidents.
Browse by Category
Planning Mistakes
Decisions that seem fine until they're not
Deployment Mistakes
The person who set this up is gone
Operations Mistakes
The ones that wake you up at night
Emergency Mistakes
The fixes that make things worse
Top 10 Quick Hits
"We'll document it later"
You won't. And then someone leaves.
"One wildcard covers everything"
One compromised key exposes everything.
"The CA emails us before expiration"
They do. To an inbox nobody checks.
"Self-signed is fine for internal"
Until you need to revoke it and can't.
"We don't need multiple CAs"
Entrust customers learned otherwise in 2024.
"Just install the cert, it's easy"
Missing chain, wrong server, wrong cert.
"We renewed it, why is it still broken?"
Renewal is not deployment.
"We'll automate eventually"
Manual processes with no documentation in the meantime.
"IT owns all certificates"
DevOps has deployed hundreds you don't know about.
"Let's just disable certificate validation"
The temporary fix that becomes permanent.
Why This Guide Exists
These aren't hypothetical scenarios. Every mistake listed here has caused real outages, real security incidents, and real late-night pages. The goal isn't to scare you - it's to help you recognize the patterns before they become your problem.