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Over the past several decades, a growing body of evidence suggests that a subset of substance users suffers from what appears to be a more chronic condition, whereby they cycle through periods of relapse, treatment reentry, incarceration, and recovery, often lasting several years. Using data from quarterly interviews conducted over a 2-year period in which 448 participants were randomly assigned to either an assessment only condition or to a Recovery Management Checkup (RMC) condition, we looked at the frequency, type, and predictors of transitions between points in the relapse, treatment reentry, and recovery cycle. The results indicated that about one-third of the participants transitioned from one point in the cycle to another each quarter; 82% transitioned at least once, 62% multiple times. People assigned to RMC were significantly more likely to return to treatment sooner and receive more treatment. The probability of transitioning to recovery was related to the severity, problem orientation, desire for help, self-efficacy, self-help involvement, and recovery environment at the beginning of the quarter and the amount of treatment received during the quarter. These findings clearly support the wide spread belief that addiction is a chronic condition as well as demonstrating the need and effectiveness of post-discharge monitoring and checkups. The methods in this study also provide a simple but replicable method for learning more about the multiple pathways that individuals travel along before achieving a prolonged state of recovery.