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in reply to Playful Perl
Add a perl script to his ~/.shellrc that searches through the users home directory for a random known text file .txt,.c,.h,.pl,whatever..and uses regular expressions to mess with the file and save it...might take awhile for him to notice the bugs, and you could make it semi intelligent ie if it's a .c have a special subset of regular expressions to chose from that wont effect the program in anyway that it will break it from compiling (ie choose a random var and change its name).
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