Many inmates use their time in jail to get clean off drugs and get their lives on the right path. Others, however, simply can’t wait return to the dangerous lifestyle of the streets.

While Boston, Massachusetts maintains its colonial past, it's ranked as one of the world's leading metropolitan areas for education and innovation. In the heart of downtown, however, is a reminder that not everyone is on the right track. In this hour: an old school bank robber maintains his swagger; an inmate with an imaginary friend proves to be a challenge for the jail, and a shocking act lands his sister behind bars, as well.

Inmates at the Suffolk County Jail look forward to mealtimes, often for reasons that have nothing to do with the food. Watch how jail dining hours erupt into chaos on this episode.

Boston, Massachusetts is by any standard a world-class city. But ever since its colonial days, some have called it a fighting town. And located in the heart of the city is a place for anyone who does their fighting outside a ring. More than 12,000 people a year pass through the doors of Boston's Suffolk County Jail. And with an average daily population of 2,700 male and female inmates, someone reaches their boiling point virtually every day of the week. For those inmates all too willing to throw a punch... the jail has a special place: The Box. As one inmate says, "Separated from everything so you learn to deal with it. It's called 'The Box Life'."

An inmate attempts to change his reputation. Another inmate, desperate for a transfer, acts out with his urine and feces. A man awaiting trial for possession of child pornography receives a visit from his daughter.

In prison for the murder of a lottery winner, Dee Dee Moore discusses her hopes for the future - including a Disney-style fairytale wedding.

Over the past ten years, the structure of local gangs has changed and that's had a serious impact on the Suffolk County jail. In this hour: an inmate takes his fights from the street to the halls of the jail, and his boyhood friend follows his example; two brothers turn to crime to support their habits, and now one faces the prospect of hitting the streets again.

While facing the consequences of dealing drugs, Michael Garcia re-evaluates his outlook on life, developing a connection with God and strengthening his relationship with his family.

Jason Flores was the victim of a horrible crime as a child. Now an adult, serving time himself, he is surprised to meet up behind bars with the man who raped him as a child. He tells us what happened....

Ex-couple Rosanna DiMauro and Kasey Ackerman plead not guilty to a violent crime in which a man was burned alive. Watch as they explain their sides of the story.

In this hour, an inmate with a long record runs an extortion scheme, while drugs inside the jail pose a lethal threat. And the jail's newest team member makes her presence known.

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