Outlook closing in offline mode

I have a laptop here that will not access Outlook when the user is trying to use it at home/ unnetworked.  It says it is unable to connect to the Microsoft Exchange Server and gives him the option of retrying or working off line. He has tried both but it comes up again saying it is unable to connect and closes Outlook down.  This is a new issue, he has not had a problem operating it this way previously.

I assume that he has usually been able to kick into offline mode and work from there or tunnel in via his VPN. I will be looking at his VPN to ensure adequate connectivity to the network from home. But the working offline part confuses me. I have never seen it close down like that.