Piper Kerman begins her memoir by describing the flight she took where she smuggled drug money across borders. She discusses how she was intrigued by her jet-setting girlfriend, and was ultimately drawn into the drug trade. She goes to Federal prison for this crime a decade later. At first she believes her case is unusual, but she begins to relate to the other prisoners. There are a few political statements about the effects of the War on Drugs, the inconsistencies in sentencing, and the unequal conditions of different prisons. Mostly Kerman describes her life in prison with some humor and a lot of self-reflection.