Dropout from addiction services is common, and strategies to improve retention represent potentially important opportunities for quality improvement and treatment effectiveness. Identification of pretreatment predictors of dropout has not led to advances in treatment delivery. Via telephone monitoring, we examined the feasibility and predictive validity of weekly assessment of psychological distress and treatment satisfaction as factors potentially associated with retention and engagement over the initial 8 weeks of treatment. Participants included 107 addiction treatment patients, of whom 78% met criteria for 4 weeks of engagement and 59% were retained for 8 weeks. Of 8 weekly assessments, 63% of participants completed six or more calls. Baseline distress, baseline satisfaction, and change in distress over 4 weeks were not related reliably to treatment dropout or engagement. Decrease in satisfaction was significantly but modestly associated with low engagement. Implications for applications of weekly monitoring to improve retention are discussed.