OK, so I saw a lot of posts from people having this problem, and had a hard time finding the answer. So, following my most recent process of blogging about it if it took me too long to figure out, here’s the answer.
We were getting a certificate error trying to connect Outlook 2007 over HTTPS connections back to our SBS 2003 Server. Have done this lots of times with XP and Outlook 2003 and 2007. Always works like a charm.
We added the certificate as usual, but still were receiving errors about the certificate not being trusted. Looking carefully I realized it was a root certificate authority error (we generated our own internal certificate for access).
So, I had to copy the certificate that had been added and paste it into the trusted root area.
Here’s the specifics:
1. Run certmgr.msc from the start menu
2. I found my exchange server certificate added in the “Intermediate Certification Authorty/Certificates” directory.
3. Select it and right-click on it, and copy.
4. Then go to the “Trusted Root Certification Authority/Certificates” directory, and right-click on the folder and paste.
5. Close the certificate manager, and open outlook and you should be prompted for credentials.
Hope this helps someone else!