One major flaw in the premise
Sly's job is to test prison security. Fine.
His way of doing so is by demonstrating he's ability to escape them. Fine.
Okay but how does that "help" the prison in terms of improving their security? Sure they can fix that "one" problem Sly figured out/exploited to get out. But does that mean if he were to put him in the prison again he would not have been able to break out ever again?
If so then how'd they know if they don't try it again and again and again,(maybe they did, but that seems hardly plausible since everyone would be in on the trick by then and things would get unnatural.)
Sly's whole business works better as a magic show, show rather than explain. Rather help solving, it's just showing them what they did wrong.
Anyone else felt that was weird?