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If you recruit prisoners to help you, they all have to escape, or else the achievement won't unlock.
and yeah, i know they too have to escape to get the achievement..
right now i'm coming to the point to just cheat the achievement to get it over with..
Hmm don't know why its not unlocking for you, i got mine by escaping from my most recent prison (~350 pop, 0 escapes in ~100 days) took just short of 2 days to incite a massive riot (apparently my prison wasn't quite as stable as i though) and me/my group made a run for it.
Regarding difficulty, I just finished perfecting the game over the last week, and the real challenge is the Polariods/Game Bible pages.
Those are a grind/annoyance beyond belief, but it is doable without having to cheat, if you put your mind to it.
Feels good to know you did it 100% legit, instead of taking the easy way out, like the supposed 100% achievement guide that just tells you to edit game files...
I uploaded my prison on the workshop for others to try. Its not perfect, its my first prison after all, but maybe its interesting for others.