The State of Oregon has operated an early prison release program called Short-Term Transitional Leave (STTL) since 1989. The program was designed to improve prison releasee reentry planning and reintegration in the community. In the last 10 years, Oregon expanded STTL several times, with individuals now being released up to 120 days early. We assessed whether differences in recidivism existed between STTL and those completing their planned sentence and if the length of their leave is associated with differential recidivism. We used propensity-score matching (PSM) to create quasi-experimental models. The results indicate no appreciable observed associations between STTL and rearrest, reconviction, or reincarceration. However, there were higher rates of technical violations among STTL participants, especially for those with the longest release time.