Earlier quoted context omitted.
That's a violation of various computer misuse laws. Get him to file a police complaint.
How is that a violation? I assume the school actually owns the laptop, and the monitoring is disclosed up front.
They can certainly have limits on what the laptop could be used for etc. and perhaps filter traffic. Possibly even track the URL's (depending on what the contract says). But reading personal emails will definitely be illegal.
When I go into a company to investigate one of their employee's you have to be very careful not to go near any personal email etc.