Some of our remote users see a security alert pop up when they use Outlook 2007 and connect to our Exchange server over the internet. Our Exchange 2007 server uses a self-signed certificate and this has been working great for many years. We just need to import the certificate in IE and that's it.
The certificate information shows it is issued to *.ssldomain.com / Trustwave and I don't know where that comes from. Our own certificates show up just fine under the Trusted Rood Certification Authorities in IE and everything else works just fine.
We tried to install this problem certificate, shows it installed fine but the message returns the next time Outlook is opened. Outlook can sync just fine with our Exchange server but the security alert is annoying. Remote computer is Windows 7 with IE10.
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That said, if you use a self-signed certificate with Exchange, you're going to have some issues with it for a while. Spend a little money getting a valid 3rd Party SSL SAN cert and you'll have fewer headaches to deal with (like making people install the certificate).