In my new and revised prison part of my project. MC is a prisoner, while his accomplice is disguised as a guard. How would the accomplice going around fooling guards? He is an excellent spy, one of the best in his world, but the same can't be said about his skills as a CO (in the name of having a flaw, making it interesting, and not being a gary sue). Nonetheless, I want to show that he has managed to fool the COs into thinking he is a CO himself, thanks to his skills as a spy. Meanwhile, those who are smart or simply unlucky enough to find out who he truly is are given a personal visit where he has them killed taken care of. No matter how ruthless he is at keeping other inmates in line, he uses all of his power to protect the MC from harm, whether that be from guards or other inmates. Along with visits from his younger brother. This still gives the other guards suspicion, but what are some things he can do to avert that suspicion besides silently killing them? Not to mention, my MC gets life. But when he escapes, he is supposed to have enough experience to become a better criminal. So much better, that he eventually escapes the country he's in and the government can't find him.
There is a long (and highly politically flammable) article in Mother Jones on the private prison industry and how easy it is to get a job there. I'm going to spoiler-wrap the link and put my hat on preemptively: No one should even think about making this thread a debate on the morality of private prisons. Spoiler: Article about private prisons in the US. My Four Months as a Private Prison Guard Basically though, depending on which prison he wants to infiltrate, he might be able to just get hired there without too much hassle.
I also think it really depends where - in America or the Uk or pretty much any first world country your chances of walking in off the street with light disguise and a forged ID are going to be nil (unless you get hired of course), in a third world type dystopia with a high turn over of guards coming and going from an occupying military, your chances would be better
