This is a problems that I have been fighting with for a while now.
The majority of our users connect remotely via a VPN connection. Many of these users report that they have trouble getting Outlook to connect when they first come in in the mornings. No remote users are set to use cached mode, and "manually control connect state" is checked to force a connect to the server. This is not an issue of Outlook defaulting to "offline" mode; it gives an error message stating that the server is unavailable.
I know it is not a VPN issue. We use Radmin, a remote access program, to remotely administer these PCs over the VPN and whenever someone contacts me with this problem I am able to connect to them fine. They tell me that usually after an hour or two they are able to connect and they don't have problems for the rest of the day.
I'm at the end of my rope with this one - it seems to be random who it affects and who it doesn't, and I have been unable to find any possible cause so far. Any help will be GREATLY appreciated.