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A while back, we set up an internal microsoft certificate server to issue certificates to our internal servers. However, when a certificate expires, we do not realize it until we start getting errors in our applications.

Is there a way to set up the certificate services to generate e-mail notifications when certificates are about to expire?

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For our external servers we use AlertFox:

I think you can recreate this setup internally with the free iMacros Firefox addon via its command line interface. Basically you create a macro that browses your website, and if the certificate is expired it will trigger an error message. That can also be combined with Nagios etc.

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I'm not familiar with that software, but if you can't find a built in method for monitoring certificate expiry, look into check-expire: It's for a Unix environment, so if you lack any compatible OS installs, you could try looking into running it under Cygwin or MinGW.

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