Most prisons here in the U.S. built after the 1960s or so, are surrounded only with chain-link fencing. If said perimeter fence isn't monitored and guarded (and/or electrified), there's nothing to stop people from scaling or knocking said fences down. Once outside of the buildings where the inmates are housed- which admittedly might take some doing- I can't imagine it would be that difficult to get past the fencing.
Getting out of the housing units would be trickier, but do y'all really think a couple of hundred men couldn't figure out a way to bust through a few metal doors? It would take time and a lot of muscle power, but it's entirely possible.
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