For many individuals, substance use leads to a chronic cycle of relapse, treatment reentry, and recovery, often lasting for decades. This study replicates earlier work, documents the transition patterns within the cycle during a 3-year period, and identifies variables that predict these transitions. Data are from 1,326 adults recruited from sequential admissions to 12 substance abuse treatment facilities in Chicago, IL, between 1996 and 1998. Participants were predominantly female (60%) and African American (88%) adults. Participants were interviewed at intake, and at 6, 24, and 36 months post-intake follow-up rates ranged from 94% to 98% per wave. At each observation, participants' current status in the cycle was classified as (1) in the community using, (2) incarcerated, (3) in treatment, or (4) in the community not using. The transitional probabilities and correlates of pathways between these states were estimated. Over 83% of the participants transitioned from one point in the cycle to another during the 3 years (including 36% two times, 14% three times). For the people in the community, about half remained in the same status (either using or abstinent) and just under half transitioned. The majority of people whose beginning status was incarceration or in-treatment also transitioned by the end of the observation period. While there was some overlap, predictors typically varied by pathway and direction (e.g., using to not using vs. not using to using). These results help demonstrate the need to adopt a chronic vs. acute care model for substance use. While exploratory and observational, several of the predictors are time-dependent and identify promising targets for interventions designed to shorten the cycle and increase the long-term effectiveness of treatment.