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At ex-work, SSL certificates expiring was probably #3 in the list of reasons for services being unavailable. It's a really easy thing to overlook in service monitoring.

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When I was a contractor, this happened to one of my customers that was under contract (I set up the cert initially). I fixed the issue overnight without major impact, but boy was I embarrassed by the bush-league mistake.

Since then, in addition to service monitoring, I've taken to calendaring certificate expiration dates ~14 days before they expire. Low tech but I've never forgotten since.

Note to self: Compulsively add every certificate expiry as an event on my calendar.

Better yet: set up a Nagios (or your site's equivalent) watcher for the expiration.

Example: http://exchange.nagios.org/directory/Plugins/Network-Protoco...

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