if they connnect using VPN, then can access some intranet service but expect intranet sharing and web shopping
as long as CC wanna know, they can easily know the account is used from which IP now
and the email content will be possibly surveilled by school, it is not a matter of tech. , just a matter of admin regulation, in anther words, they want to do it or not.
but normally i think all CC actions are triggerred by a complain, hehe, no complain, all fine :P