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Might be easier to use software to TRACK what he does, rather than stop it. And use another form of punishment when he violates their "trust". They could probably put some sort of tracker on at the network level if they have it set up that way (the way companies do). But you'd know more about that than I do.
But in terms of teaching the kid something, forcing him to make the right choices (correcting him when he makes poor choices) rather than making the choices for him will teach him more.
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