[jcrawfordor]

In my small organization we had planning and multiple reminders to renew the cert well before it expired, and we did. Due to a miscommunication between myself and a coworker, the new cert sat ready for nearly two months without ever being added to the configuration (we were both certain the other had done it, naturally).

There's a remarkable number of ways for this simple thing to go wrong. To prevent a future repeat, we got rid of our calendar reminders (which we started ignoring once we both thought the change had been made) and wrote a script that emailed us based on the time to expiration of the live cert. This is a much better method.

Of course, give us enough years and I'm sure we'll manage to find a way to get this new setup wrong.