That Time a Certificate Took Down Production: A DevOps Trauma Bond

We All Have "The Incident"

Ask any DevOps engineer about their worst certificate story and watch their face change. The thousand-yard stare. The nervous laugh. The "oh god, that day" head shake.

Mine was February 2019. 3 AM. My phone buzzing like an angry hornet. Production down. Not just our app—everything. The API, the admin portal, the status page that was supposed to tell people about outages.

The certificate had expired 37 seconds ago.

The renewal script had been failing since January 3rd. The alerting was configured to email tom@company.com. Tom left in 2017. Nobody created an alias. The logs were writing to a disk that filled up in December.

I fixed it in pajamas and shame while the CEO asked questions I couldn't answer.

We don't talk about February 2019.

The Certificate Trauma Collection

"The One Where We Lost a Customer"

From Rachel, SRE at a fintech startup:

"Our biggest client was doing their quarterly security review. Super strict about compliance. Of course, that's when our customer portal certificate decided to expire. Not at midnight like a civilized certificate. At 2:17 PM. During their review.

The customer's security team screenshots the browser warning. Emails their executives. Uses words like 'critical security failure' and 'unacceptable risk.'

We renewed it in twelve minutes. They terminated our contract in twelve days.

The certificate? It was for a staging environment. That we forgot existed. That was somehow accessible from their IP range. That nobody used except during security reviews."

"The Recursive Dependency Hell"

From Marcus, Platform Engineer:

"We had bulletproof certificate automation. Monitored by Prometheus. Prometheus secured with certificates. Those certificates managed by Vault. Vault's certificates managed by our automation. Our automation authenticated to Vault using... certificates.

Can you see where this is going?

One expired certificate started a cascade. Automation couldn't authenticate to Vault. Vault couldn't issue new certificates. Monitoring couldn't alert because its certificates were expired. The dead man's switch? Also certificate-protected.

We call it Certificate Ouroboros. We fixed it with console access and tears."

"The Weekend Wedding Special"

From Alex, DevOps Lead:

"My colleague was getting married. Beautiful destination wedding. No phone coverage. We all knew. We prepared. We had runbooks. We had backups for the backups.

The certificate that expired wasn't in our inventory. It was for an internal service that nobody knew used HTTPS. But our main app had a hard dependency on it. At startup. Which happened during our Saturday deployment.

The groom fixed it from his honeymoon suite while his new spouse questioned their life choices.

He still flinches when anyone mentions certificates."

"The Printer Incident"

From Jordan, Systems Engineer:

"A network printer took down our entire authentication system. I'm not making this up.

Some genius years ago decided the printer needed a web interface. With HTTPS. With a certificate from our internal CA. The printer firmware couldn't auto-renew. Nobody documented this.

When it expired, it started hammering our LDAP server with auth requests. Thousands per second. LDAP crashed. Nobody could log into anything. VPN, email, door badges—all dead.

Six hours to trace it to a printer. A PRINTER.

We now have a spreadsheet called 'Devices That Shouldn't Have Certificates But Do.' It has 47 entries."

"The Time Zone Disaster"

From Sam, Infrastructure Engineer:

"Our certificate expired at midnight. We knew this. We scheduled the renewal for 11 PM. Foolproof.

Except the server was in UTC. The renewal script used local time. The monitoring was in Eastern. The certificate authority was in Pacific.

It expired at what we thought was 7 PM. The renewal ran at what it thought was 11 PM. Which was 3 AM the next day. Seven hours of downtime because nobody agrees what time it is.

We now use only UTC. For everything. My calendar looks insane but at least certificates renew."

Why These Stories Are Universal

It's Always the Forgotten System

Nobody's production web server certificate expires anymore. We monitor those obsessively. It's always:

• The internal wiki from 2016
• The IoT device someone connected once
• The test server that became critical
• The vendor appliance with a web interface
• The thing labeled "temporary" three years ago

The Documentation Is Fiction

Every certificate horror story includes someone saying "according to the documentation..." followed by hollow laughter.

The wiki says the cert is at /etc/ssl/certs. It's actually at /opt/custom/app/security/keys/new/final/. The renewal instructions reference servers decommissioned during Obama's first term. The contact person is "admin."

The Timing Is Sadistic

Certificates don't expire on boring Tuesday afternoons. They expire:

• During board presentations
• On holidays
• During migrations
• While you're at the dentist
• The day after you said "our infrastructure is rock solid"

It's like they know.

The Fix Is Always Temporary

"We'll just manually renew it this once."
"Quick workaround for now."
"We'll automate it properly next sprint."

Three years later, that "temporary" fix is load-bearing infrastructure held together by cron jobs and hope.

The Shared Trauma Response

Every DevOps team develops the same coping mechanisms:

The Paranoid Calendar: Seventeen different reminders for each certificate. Email, Slack, text message, carrier pigeon. All set for a week before expiration. Nobody trusts automation anymore.

The Ceremony: The ritual checking of certificates every Monday morning. Opening each site. Clicking the padlock. Muttering "good, good, still valid." It's not rational. It's necessary.

The Stories: We tell these tales to new hires like ghost stories. "Gather 'round and let me tell you about The Great Certificate Expiration of 2018..." It's partly warning, partly therapy.

The Overcorrection: One expired certificate and suddenly you have monitoring for your monitoring, alerts for your alerts, and a runbook that rivals War and Peace.

Why We Keep Doing This to Ourselves

We're smart people. We automate everything else. We have sophisticated deployment pipelines. We use machine learning for capacity planning.

But certificates? We're still running bash scripts written by someone who left three years ago.

Because fixing it properly means admitting we've been doing it wrong. It means explaining to management why we need to spend three sprints on something that "already works." It means acknowledging that our home-grown certificate management is held together with digital duct tape.

So we patch. We workaround. We add another monitoring check. We tell ourselves we'll fix it properly "next quarter."

Then 3 AM comes. The phone buzzes. And we create another story for the collection.

The Universal Truth

If you've been in DevOps for more than two years and don't have a certificate horror story, you're either lying or lucky. Probably both.

These aren't just war stories. They're warnings. Every "that could never happen to us" is followed, eventually, by "how did this happen to us?"

Your certificate horror story isn't a matter of if. It's a matter of when.

The only question is: Will it be original enough to share at DevOps meetups?

Breaking the Cycle

Maybe it's time to stop collecting these stories. Maybe it's time to admit that certificate management isn't something we should be building ourselves. Maybe it's time to let someone else stay up at 3 AM.

But until then, we'll keep swapping tales of certificate disasters. Bonding over our shared trauma. Adding new chapters to the anthology of "things that shouldn't have expired but did."

Because every DevOps team has that one certificate story.

What's yours?