Corrected entry: The Jailbird is supposed to be state of the art super max facility, but the guards don't scan the prisoners for pins, which some of the prisoners use to escape from their handcuffs.
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Correction: Cyrus had a pin inserted into his hand. There is no way to scan for that. Pinball had something in his stomach. They had concealed their means of escape very well. Not even a plot hole if they didn't scan for it anyway, just a human mistake to not see something that is concealed.
lionhead