One answer to that is that prison bureaucrats shouldn't be in charge of deciding stuff like this.

Except that whoever you replace the bureacrat with to be in charge, then becomes a defacto bureaucrat themselves with all the same incentives and disincentives. So the situation remains unchanged.

lets get a buncha folks who have no idea about prisons, prisoners, and in most cases technology, and have them make decisions about how to handle sociopaths and technology.

that would only get ugly.