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Many of the 2.2 million people incarcerated in the U.S., participate in prison-based programming or employment. I use Boston Reentry Study data (n=122) and interviews with a convenience subsample (n=28) to examine how recently incarcerated individuals describe their motivations for participation and experiences in prison-based activities. I find that imprisoned individuals strategically participated in programs and jobs to address the immediate conditions of incarceration and preserve a sense of autonomy. Most respondents indicated that activities were only somewhat helpful to them, due to insufficiently trained facilitators or misaligned content. These findings add to existing research on in-prison programs and jobs and point to considerations, in addition to recidivism and employment, that may be of interest to researchers and policy makers.