Why Every DevOps Team Has a Certificate Horror Story

The Certificate That Ruined Christmas

It was December 23rd, 4:47 PM. Sarah was halfway through her third glass of office party punch when her phone exploded. Production was down. Not slow. Not degraded. Dead.

The wildcard certificate had expired.

The one that covered *.api.company.com, *.admin.company.com, and seventeen other subdomains nobody documented. The renewal script? It had been failing silently for six weeks. The logs? Rotated into oblivion. The person who wrote it? Left for greener pastures in October.

Sarah spent Christmas Eve on a Zoom call with three other engineers, manually generating certificates while the CEO asked "how did this happen?" every fifteen minutes.

Every DevOps team has this story. The details change, but the pain is universal.

The Museum of Certificate Disasters

The Demo Day Special

Picture this: Your CEO is presenting to potential investors. Big screen. Lots of money in the room. Click to the product demo and—browser warning. "Your connection is not private."

Turns out that staging environment you spun up six months ago for "just this one demo"? Its certificate expired yesterday. The renewal was handled by Gary's laptop. Gary's in Bali. Gary doesn't check Slack on vacation.

The CEO improvises. The investors are "concerned about technical operations." You update your resume.

The Acquisition Surprise

Your company just acquired a smaller competitor. Congratulations! You now own:

• 47 domains nobody has a list of
• Certificates from three different CAs
• At least six that expired last year but "the sites still work somehow"
• A WordPress multisite with a cert that expires tomorrow
• No documentation

The previous team's solution? A spreadsheet on someone's desktop titled "certs_final_FINAL_v2_actually_final.xlsx". It was last updated in 2021.

The Prometheus Punishment

You built beautiful monitoring. Prometheus, Grafana, the works. Alerts for everything. CPU, memory, disk space, network latency, even that custom metric for coffee machine status.

The monitoring certificate expired on Tuesday.

Nobody knew because... the monitoring was down.

The Load Balancer Lottery

Three identical load balancers. Same config. Same automation. Same certificate renewal script.

Two renewed perfectly. The third didn't.

Why? Nobody knows. The logs show success. The script returned 0. The old certificate is still being served. You check everything twice. Time zones? Permissions? Phase of the moon?

Four hours later you manually replace it and add "investigate later" to a ticket that will never be investigated.

The Forgotten Fleet

That certificate scanner you ran last month found 73 certificates across your infrastructure. You manage 12 of them. The others?

• The printer management interface (apparently it has HTTPS?)
• Bob's development VM that's somehow internet-facing
• A Grafana instance from a hackathon three years ago
• The old CEO's vanity project that "we're definitely shutting down next month" for the past two years
• Something called "test-server-do-not-delete-important"

Half expired already. The other half expire next month. None are in your renewal automation.

Why This Keeps Happening

We're smart people. We automate everything. We have CI/CD pipelines that would make NASA jealous. So why do certificates keep biting us?

Because certificate management exists in the gap between "too important to ignore" and "too boring to do right."

It's not exciting like Kubernetes. It's not trendy like observability. It's just... certificates. So we cobble together the minimum viable solution and promise to "revisit this next quarter."

Next quarter never comes. Until 4:47 PM on December 23rd.

The Universal Constants of Certificate Pain

Every certificate horror story shares the same elements:

It's always the one you forgot about. Never the main production cert you monitor obsessively. It's the Jenkins box. The VPN appliance. That API endpoint only accounting uses.

The person who knows is gone. They left for a startup. Or they're on parental leave. Or they just forgot because they set it up three years ago after four beers at the company offsite.

The documentation lies. If it exists at all. That runbook? It references servers that were decommissioned in 2020. The wiki page? Last updated by an intern who "thinks this is how it works."

It happens at the worst possible time. During the big demo. Black Friday. When you're on vacation. When the senior engineer is at a wedding. Murphy's Law was written about SSL certificates.

Breaking the Cycle

Here's the thing: we've all tried to fix this. We've written the scripts. Built the automation. Created the runbooks. Set up the monitoring.

But maintaining certificate infrastructure isn't your job. It's a distraction from your actual job. You didn't become a DevOps engineer to babysit OpenSSL.

That's why we keep having these disasters. We treat certificate management like a side project instead of the critical infrastructure it actually is. We wouldn't run our own power plant. Why are we running our own certificate authority?

Your Horror Story

Every DevOps engineer reading this is nodding along, remembering their own certificate disaster. The one that ruined a weekend. Or a holiday. Or a career.

Maybe it's time to stop collecting these war stories.

Maybe it's time to let someone else worry about whether the certificate renewal script will work next month.

Maybe it's time to stop playing certificate roulette and admit that some problems are worth paying someone else to solve.

But until then? Check your certificates. That Jenkins box is probably expiring next week.