Originally Posted by pittpanther

The fact that my company is using an MS Exchange server means I cannot just decide to switch to Thunderbird, etc. I was led to believe that it's Outlook only.

I always use a VPN to connect to my company, as I work from home when not on the road. We used to use the Checkpoint VPN. Always worked from home - I mean 100% of the time. Also worked from most hotels. Every once in a while, there would be a hotel where Outlook would not connect. The VPN seemed to connect fine, but Outlook would never connect and sync. This is with a VPN. Exact same connection method used at home. For example, I stayed at the Marriott Courtyard in Edmonton probably a dozen times - never got an Outlook connection while staying there. Always had to use Web-based mail.

Any ideas as to what the hotel ISP could be doing that could block connectivity through a VPN?

We no longer use a VPN, and have now switched to PPTP connections. Have not had any problems at hotels, yet.