Avoid or evade ...
At one time in an old job for an organisation I worked for; there was a systemic rout of the 'H:' (or home) drives of any staff/students, smart to the winds of change, one promptly removed MP3's of some of my fave music.
There are times in class when you want the students to focus, either on set work or practical exercises, over the years I found that some of my less eclectic music aided the harmony. Music doth quell the savage beast (and student).
Solving this took little imagination; reasonably adept at web design and at the time quite comfortable with flash app development. I found a flash based MP3 player, that worked off of an XML file pointing to MP3's anywhere on the net. So, with some tweaks, UI adjustments and changes to the code. It was not long before I had a formidable collection on music on one of my websites (no longer there I hasten to add).
The result was; Andrew could still listen to music at his leisure and students pleasure, whilst the other staff/students were being systematically told to remove any unlicensed software from their storage areas. I don't feel I needed to be particularly covert, understanding that it would be the last place they would ever consider looking.
Remember, if you want to hide something, put it in plain view, they will never see it.