Exiting the criminalized sale of sex, which we refer to as prostitution, is a complex, recursive process which has been rarely studied longitudinally. Using typical case sampling, we selected two respondents from a two-year ethnographic study of a court-affiliated diversion program in Philadelphia who participated in a total of eight interviews. Saldaña’s (2009) seldom-used longitudinal coding method was applied to conduct a fine-grained analysis of participants’ perceptions of exiting prostitution over time, focusing on participants’ motivations and actions. Respondents managed expectations of others and themselves and their sense of self-worth within a context of changing relationships, structural opportunities, accomplishments and setbacks. Viewed in a longitudinal context, the same relationships and structural hurdles often had a different impact on women’s motivation to exit at different time points. We argue that a longitudinal perspective of the exiting process is critical to avoid erroneous binary classifications of women as either exiters or non-exiters from prostitution, as the exiting process is more complex than what cross-sectional studies have previously revealed. Findings have implications for researchers of prostitution and programs for women exiting prostitution that should structure supports and (dis)incentives in a nonjudgmental fashion in line with this nuanced understanding of exiting over time. This is particularly important in criminal justice settings, where punitive responses have serious short- and long-term consequences.