So I am deploying a new terminal server running server 08, replacing an aging 2003 TS server. On the server we've installed Office 2010. On our previous TS server, when a user first logs in and opens outlook, two things happen - cached mode is automatically turned off, and the account\profile automatically configures itself (or with a few clicks of next, but no input by the user). Cached mode is the real biggie as it tends to cause a bunch of problems here (specifically with the calendar).
So are there some settings I am missing here?