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Well, that's the last time *I* skip curfew.
Outsider prisoners are the unfortunate wastelanders who crossed one of many restrictive Vault City regulations in Fallout 2.
Any outsiders who come to Vault City are subject to its myriad laws and regulations, the slightest violation of which will earn them imprisonment in a cage in the Courtyard, as much a lesson to them, as to the rest of non-citizens.
Outsider prisoners appear only in Fallout 2.