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Former inmate Jennifer’s confession leaves Cyndi in a state of complete shock. Jun 27, 2024 · Ex-convict Jason doesn’t make the best first impression with his roommate Emily. Apr 30, 2024 · Episode 2. Across the country, these individuals are on separate journeys but share a single motivating force: to help formerly incarcerated individuals re-enter society. The news received mixed responses. Season 15 . , as they strive to overcome personal struggles, including drug "Inmate to Roommate" follows six inmates from across the country as they leave prison behind and move in with everyday people they've never met. Watch Jail Season 2. Synopsis Inmate to Roommate follows recently released inmates as they re-enter society and move in with everyday people. Season 2 Episode 6 – The Feast of Dr. Roommates Jim and Marisol have a face-to-face confrontation with inmate Mickey. 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