I think I've figured it now. You say they have to enter their password. For us it's showing the first run wizard for Outlook for them to run through...
In terms of Office365 and the move to Wave15, I notice it changes to the outlook.office365 domain and as such then uses things like smtp.outlook.com....
Probably true. But could you train them to deal with every single tech issue they'll come across? Who's going to make sure the network is running. No...