Street-based sex work that is criminalized throughout much of the U.S. diversion programs has shown mixed results. This study examined the effect a quasi-experimental intervention (prostitution diversion program, n = 149) had on prostitution rearrest compared with a waitlist control group (n = 77) among N = 226 individuals arrested for prostitution in Baltimore. In both groups, n = 64 (28.32%) were rearrested for prostitution over 30 months. Tests of differences compared groups with a significant difference in gender only. A Cox proportional hazard model examined differences in survival time (to recidivist prostitution arrest) between individuals in the control and intervention groups at 6, 12, 18, 24, and 30 months. Results indicate that participation in the intervention did not have a significant effect on decreasing prostitution arrests over time. History of prior prostitution arrest was a significant predictor (hazard ration (HR) = 1.12, p = .02) of rearrest.Lack of program success suggests that barriers to exiting prostitution are substantial, despite availability of supportive services, and that diversion programs may not be the best intervention strategy for all sex workers. Future research should identify motivators for exiting and how to reduce exiting barriers.