A growing line of research has shown positive treatment outcomes from technology-based therapy for substance use disorders (SUDs). However, little is known about the effectiveness of technology-based SUD interventions for persons who already had numerous prior SUD treatments. We conducted a secondary analysis on a 12-month trial with patients (N = 160) entering methadone maintenance treatment (MMT). Patients were randomly assigned to either standard MMT treatment or a model in which half of standard counseling sessions were replaced with a computer-based intervention, called Therapeutic Education System (standard + TES). Four treatment history factors at baseline, the number of lifetime SUD treatment episodes, detoxification episodes, and inpatient/outpatient treatment episodes were categorized into three levels based on their tertile points, and analyzed as moderators. Dependent variables were urine toxicology results for opioid and cocaine abstinence for 52-weeks. The standard + TES condition produced significantly better opioid abstinence than standard treatment for participants with 1) a moderate or high frequency of lifetime SUD treatment episodes, and 2) those with all three levels (low, moderate and high) of detoxification and inpatient/outpatient treatment episodes, ps < .01. The standard + TES condition enhanced cocaine abstinence compared to standard treatment among people with 1) a moderate or high frequency of lifetime SUD treatment episodes, 2) a high level of detoxification episodes, and 3) a moderate or high level of inpatient treatment history, ps < .01. We found that including technology-based behavioral therapy as part of treatment can be more effective than MMT alone, even among patients with a history of multiple addiction treatment episodes.