MS Outlook, Cannot connect to server

I have input my hotmail account in MS Outlook.

When I try to delete emails from Outlook, it always informs me that it cannot connect to server (without even trying).
So I check "Work Offline" and then try deleting the email again. Same problem.
However, when I uncheck it (after I have checked it) and then press delete, the email is deleted.

How do I delete emails in the normal manner rather than go thru the hassle of checking and unchecking the "Work Offline" mode?
Thanks

 

Is it possible outlook is setup to leave a copy on the server? so if you tried to delete an email it would need to connect to delete the email at the server.

 

Chuck,

There is no option to leave messages on server for the Hotmail account.

I am using MS Outlook 2003.
Thanks