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Despite being a key component of the U.S. correctional system for more than a century, parole has been an understudied issue in criminal justice policy research. This holds particularly true for the decision-making process of discretionary parole boards, especially as many U.S. states have replaced this type of prison release mechanism with mandatory parole during the past few decades. This research attempts to address this gap by exploring the case of Massachusetts, where discretionary parole is still used for inmates who are serving a second degree life sentence and who become eligible for parole after serving fifteen years. Through a content analysis of the parole board decisions made in the years of 2012 and 2013, I investigate which specific factors most impact the decision-making of the parole board members. I consider factors such as the nature of the initial crime(s) committed and the time already served but also the offender’s disciplinary record, participation in rehabilitative efforts, victim and family impact statements, and expression of remorse.