The link above at least confirms that the settings are correct in Outlook, and the issue somehow revolves around individual laptop and/or individual user configurations. Possibly related to Security Certificates in some way. I suspect the SBS 2008 server that is running Exchange has, in the past, been administered as if it were a standard 2008 server, since the WSUS configuration was broken by micro configuration changes not suitable for SBS 2008. Whatever the issue, it is not obvious, or consistent across users or versions of Outlook in use. Two users, one with the issue and one without will be using the same versions of Outlook, with the same configuration visible in the Options
I will make a post here as soon as I have some sort of resolution to this issue, and have at least a small party to celebrate as well.