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Contemporary researchers of desistance emphasize the importance of looking at desistance as a process, though measuring it as such is complicated. This paper explores the process of desistance, with a particular emphasis on those who have taken a “step back,” by relapsing, reoffending, or being reincarcerated while attempting to desist. I look at how past and current experiences of desistance “failures” shape people’s senses of self and understandings of future life chances. The paper is based on repeated interviews with men and women returning from a county level correctional facility in Massachusetts. Most had been previously incarcerated and several relapsed, reoffended, or were reincarcerated during the follow up period, though all hoped to “go straight” upon release. These setbacks were often framed as being driven by personal weakness, including addiction, materialism, and poor relationship choices. They rarely included structural barriers, in spite of this population facing significant structural challenges. I analyze how they make sense of these moments, and discuss how we, as researchers, should make sense of these ‘failure’ stories to better understand the concept of desistance.