If there is any entitlement involved it is in the hands of the paying party being entitled to make decisions about type of usage.
The student is, in almost every case, a paying party as well... When they sign up for their education, there is almost always a fee included for the "free" internet provided by the school. I'm just saying, I need to check Mail, as that's where my school's mail arrives, but it was blocked, does that make any sense to you? I got someone from my school's HELP DESK to bypass the block on Mail. However, I DO understand that you are not allowed to access any warez sites like rapidsh*re or torrents and what not... If thats the goal of using FreeGate than I agree that the school is 100%, wait, make that 200% correct.
And at least you had the decency to respond in a mature way, instead of just sending people off without discussion, like the first reaction.
(Furthermore I would like to clarify my idea of "legal sites"- I'm a student Graphic Design, I need stock and fonts, however, even certain website containing these resources are blocked, perfectly legal websites that offer royalty free stock and free for use fonts.)