An anonymous reader writes "We're a school district in the beginning phases of a laptop program which has the eventual goal of putting a Macbook in the hands of every student from 6th to 12th grade. The students will essentially own the computers, are expected to take them home every night, and will be able to purchase the laptops for a nominal fee upon graduation. Here's the dilemma — how much freedom do you give to students? The state mandates web filtering on all machines. However, there is some flexibility on exactly what should be filtered. Are things like Facebook and Myspace a legitimate use of a school computer? What about games, forums, or blogs, all of which could be educational, distracting or obscene? We also have the ability to monitor any machine remotely, lock the machine down at certain hours, prevent the installation of any software by the user, and prevent the use of iChat. How far do we take this? While on one hand we need to avoid legal problems and irresponsible behavior, there's a danger of going so far to minimize liability that we make the tool nearly useless. Equally concerning is the message sent to the students. Will a perceived lack of trust cripple the effectiveness of the program?"