Outlook does not automatically detect connection state

[CPSMichele]

I am running Outlook 2003 on Exchange 2003. I am not using cached mode and
use online & offline only.

My issue is that when I choose the option to auto detect the connection
state when starting, it does not. In fact when I choose the option to
manually detect the state, it won't even prompt me to choose the connection
state.

To get around this, I have to reboot my laptop whenever I undock it from the
network in order to start Outlook in online mode again.

Any ideas?
Thank You.