My Boss is able to take his laptop to any internet connection and Outlook will successfully connect to our Exchange 2010 server - that is except for the connection at his house. For what it's worth his ISP is Bresnan. When he attempts to connect, a certificate error pops up (attached to this thread). The certificate error that pops up is issued to bresnan.net, Outlook should be pulling a certificate issued to our domain that we purchased from GoDaddy.
I have spent several hours on support calls with Microsoft, and they say it's an issue with Bresnan. I tried to get support from Bresnan, but they were even less help.