The fact that Randy has logged on has now been recorded by the system in several locations on the hard drive. He has, in other words, just slapped big greasy fingerprints all over a weapon that the police are moments away from seizing as evidence. If Tombstone is shut down and grabbed by the cops before Randy can erase those traces, they will know he has logged on at the very moment that Tombstone was confiscated, and will put him in prison for tampering with evidence. He very much wishes that Douglas MacArthur Shaftoe could somehow be made aware of what a ballsy thing he is doing here. But then Doug has probably done all kinds of ballsy things of which Randy will never be aware, and Randy respects him anyway because of his bearing. Maybe the way to get that kind of bearing is to go around doing ballsy things in secret that somehow percolate up to the surface of your personality.