This one kicked my ass for the last 24 hours.

Basically what it boils down is is this: If you create an self signed certificate using the selfssl.exe tool from the IIS Resource kit to install a certificate for a web site in IIS, when that certificate expires, you will no longer be able to connect to your SQL Server. Here are a few things to avoid this problem:

  • If you do create a certificate in the manner, make sure that you set the expiration for something very far in the future. Think /t:3650 (10 years).
  • If you have a cert that causes connections to fail, don't think that creating a new one solves the problem. You have to go back and delete the old cerficates out of your certificate store or SQL Server will still find it and still disallow connections.