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WebOps DeskSite security, plainly
01 · Availability · 10 min

Certificates: the outage you can put in your calendar

An expired certificate is the only outage that sends you the date in advance. It still takes sites down every week.

WebOps Desk editorial teamHow these are written Updated on
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The outage that arrives on schedule

Almost every failure in operations is a surprise. Certificate expiry is not: the date is written into the certificate, visible to anyone who looks, months in advance. It still takes sites down constantly, which tells you something about how monitoring is usually set up.

The failure mode is also unusually severe. Browsers do not show a degraded page; they show an interstitial warning that most visitors will not click through.

Automatic renewal is not the whole answer

Automated issuance has made renewal routine, and it has also made people stop watching. Automation fails quietly for ordinary reasons, and nobody notices until the certificate actually expires.

  • The validation check fails because a DNS record or a redirect changed.
  • The renewal ran but the new certificate was never deployed to the server that serves traffic.
  • One host in a load-balanced set renewed and another did not.
  • A certificate on a device or appliance was never part of the automation at all.
  • The intermediate chain changed and was not updated, so some clients fail while browsers appear fine.

What to watch

Beyond the expiry date
CheckWhy
Days remainingThe obvious one; alert well before the last week
Chain completenessAn incomplete chain fails for some clients only
Hostname coverageSubdomains and alternative names are often forgotten
Every endpointLoad balancers, staging, APIs, mail servers
Protocol and cipher supportDeprecations break older or newer clients
Renewal job healthFailing automation is the real early warning

Keep an inventory

Most organisations have more certificates than they think: the main site, an API, a staging environment, a mail server, an appliance in a cupboard. The one that expires is usually the one nobody remembered owning.

A short list, with an owner and a renewal method per entry, reviewed twice a year, prevents almost all of these incidents.

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