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Justice-involved individuals with alcohol and drug use problems reoffend at higher rates than their nonusing counterparts, with alcohol and drug use serving as an important vector to recidivism. At the daily level, exposure to stressors may exacerbate problematic alcohol and drug use; at the individual level, prior treatment experiences may mitigate substance use as individuals adapt to and learn new coping mechanisms. We conducted a daily diary study using Interactive Voice Response technology over 14 consecutive days with 117 men on probation or parole participating in a community-based treatment program (n = 860 calls) and referred to medication-assisted treatment. Participants reported daily stressors, craving for alcohol and illegal drugs, and use of alcohol and illegal drugs 1 time each day. Results of multilevel models showed significant day-to-day fluctuation in alcohol and drug craving and use. In concurrent models, increases in daily stressors were associated with increases in cravings and use of illegal drugs. Prior treatment experience modified many of these relationships, and additional lagged models revealed that those with less treatment experience reported an increase in next-day alcohol craving when they experienced increases in stressors on the previous day compared to those with more treatment experience. Collectively, these findings highlight the importance of tailoring treatment as a function of individual differences, including prior treatment experiences, and targeting daily stressors and subsequent cravings among justice-involved adults with alcohol and drug use problems.