The concept of legal pressure has been used in research to study the effect threats of increased punishment have on the rehabilitation trajectory of individuals with substance use disorders under community supervision. This study investigates how unequal legal pressures affect the chances of success for participants in a drug court-supervised rehabilitation aftercare program. Using bivariate and logistic regression analyses, we compare the successful program completion rates of individuals charged with felony- and misdemeanor-level offenses. Consistent with the legal pressure thesis, we find that clients under misdemeanor-level charges become more likely to fail probation than those under the threat of felony-level punishment upon transition to community aftercare. Moreover, the higher rate of failure in the lower legal pressure group is strongly associated with their failure to abstain from drug use during the outpatient phase of community supervision. A shift in legal pressure is thus identified as a potential dynamic risk factor in substance abuse aftercare. The implications for community supervision of offenders recovering from addictions are discussed.