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On my mac, I looked at the Mail Connection Doctor and one of the things I noticed was an expiration date for my Parallel Panel self-signed root certificate.

Is that something I have to renew or does it auto renew itself?

I'm using a virtual dedicated server and didn't buy the certificate, it was there by default.

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To answer your question right away: No these certificates do not auto-renew. You would have to renew the certificate yourself or create a new self signed certificate on this machine (e.g. via openssl).

What you have to keep in mind however, is that an expired certificate will not lead to your website stopping to work - there will simply be a warning that the certificate is expired and you have to confirm this before the page loads. As you are using a self-signed certificate right now you already should receive a certificate warning - so even if the certificate expires nothing changes for you.

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When a self-signed certificate expires, does that mean it's no longer secure ? –  Kris May 14 '12 at 19:05
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No not per se. The certificate expiry exists to create a limit how long a certificate can be valid (given it is not revoked by the CA before). This ensures that you do not have any certificates that would be valid forever. This could be a risk if you lose the certificate/private key. Take for example someone gets access to old (expired) certificate from paypal.com and they plan to use it to phish data - your browser would warn you that this certificate is expired and you'd know something is wrong. this has absolutely nothing to do with the encryption - this is still working fine –  leepfrog May 14 '12 at 21:12
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You have to regenerate it yourself after it expires.

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They cert probably won't renew on its own. If this if your account/server, check with the VPS server provider to see what their process is.

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