Hello Darryl,
See You Receive a Target Principal
Name is Incorrect Certificate Error in Outlook 2007 When Connecting to Either POP3 or IMAP4 on SBS 2008 . It states the following:
This error is not fatal. If you choose Yes, the connection will continue successfully and securely. You will not receive this prompt again until you close and reopen Outlook 2007. This error does not occur
with earlier versions of Outlook, Outlook Express, or Windows Mail.
The problem is due to the order in which the DNS names are listed in the Subject Alternative Name field on the SBS 2008 self-signed certificate, and the way that Outlook 2007 reads this field. The first DNS name in the list does not
match the servers public FQDN (Fully Qualified Domain Name). Outlook 2007 reads only the first DNS name, and then compares it to the name of the POP, IMAP, or SMTP server that it is configured to connect to. The two names do not match.