The association between drug court clients’ pro-drug and pro-recovery social context at multiple ecological levels, and phase of recovery was assessed, and gender comparisons were evaluated. Drug courts provide alternatives to incarceration for substance abusing offenders, providing treatment within clients’ social environments. The findings indicated that social context is associated with recovery, and that this relation differs by gender. Specifically, increased favorable attitudes toward drug use among social referents were associated with men being in an earlier phase of recovery and women being in a later phase of recovery. Furthermore, perceived encouragement to use drugs was associated with being in earlier phases of recovery, while positive outcome beliefs related to recovery were associated with being in later phases of recovery. Therefore, drug courts may lead to positive long-term outcomes, as social context can be addressed during the recovery process. Additionally, these courts might benefit from incorporating gender-specific components into treatment.