Note, I have followed the Microsoft KB article: http://support.microsoft.com/kb/940726 to fix an issue with a certificate warning. However, we are still experiancing the issue. We did rebuild the certificate for external access to the server, and then we started to have this problem. Is it possible that the certificate is faulty in some way (we are using the Windows Server 2008 Certificate Authority), if so how would I confirm this?

Any reason you're using your internal CA? You need to get a cert from a third party CA. Also the work around in the article suggest you are not going with a SAN cert. It'll save you some headache if you go with a SAN cert. More on Exchange 2007 and certificates - with real world scenario http://msexchangeteam.com/archive/2007/07/02/445698.aspx James Chong MCITP | EA | EMA; MCSE | M+, S+ Security+, Project+, ITIL msexchangetips.blogspot.com

Hi cdcomp, Please note that the scenario in KB 940726 is only to Outlook Clients that connect to Exchange from inside the local network. This scenario does not apply to remote Outlook clients that connect to Exchange by using Outlook Anywhere. So if you are using Outlook Anywhere, this KB is not fit for you. For this issue, please refer to the document given by James, it is a good article. Here are some related posts for you: SSL Certificate http://social.technet.microsoft.com/Forums/en-US/exchangesvradmin/thread/425aad53-a26f-409f-8ab0-c6fdd23f5ba1 Exchange 2007 Outlook Anywhere SSL Error http://social.technet.microsoft.com/Forums/en/exchangesvradmin/thread/28348698-0949-463b-b689-0f72ba46ab75 Thanks, Evan Please remember to click Mark as Answer on the post that helps you, and to click Unmark as Answer if a marked post does not actually answer your question. This can be beneficial to other community members reading the thread.