In Austria, judges can offer quasi-compulsory treatment options (in- and outpatient settings) as an alternative to imprisonment for drug-related delinquencies. A standard assessment of medical, psychological and legal data on the implementation of health-related and legal interventions in Austria was applied in 96 opioid-dependent individuals (10.4% female) undergoing quasi-compulsory treatment, receiving health-related measures. Additional data from the official prison registry were collected (data of 228 imprisoned individuals sentenced for drug-related crimes; 14.5% female) to gain comparable information to in- and outpatient health-related measure groups. Health-related measures were offered significantly more often to individuals charged with solely narcotics possession and/or trade, whereas imprisonment was filed significantly more often when concomitant property or violent crimes were committed in addition to drug possession/dealing (p < 0.001). Both cohorts had high prevalences of previous convictions (health-related measure 84.4%, prison 93.9%). The majority of patients in health-related measures suffered at the time of investigation from severe depression (62.5%), anxiety disorders (58.3%) and had a high loading of suicidal ideation (45.8%). Women showed a higher prevalence of affective disorders (p = 0.042), with higher administration rates of psychopharmacological medication (p = 0.045), whereas male offenders scored significantly higher in violent behaviour (p = 0.004). Inpatients showed a significantly higher burden of comorbid disorders compared to outpatients and reported a higher need for psychiatric treatment and legal counselling (all p < 0.001). The inpatient sample had a longer duration of opioid use (p = 0.024), a higher lifetime prevalence of intravenous drug use (p < 0.001) and a higher rate of hepatitis C infections (p = 0.012). Results confirm that imprisonment is sentenced to a vast extent for severe crimes, and health-related measure is well accepted among judges. However, based on patients’ high loading of previous convictions and alarmingly high burden of comorbidities, quality improvement and assurance in health-related measure are required when patients have their first contact with the criminal justice system. Continuous focus on applying diversion procedures is also required to reduce societal costs. This research was published in the Drug Science, Policy and Law Journal the definitive source of evidence-based information and comment for academics, scientists, policymakers, frontline workers and the general public on drugs and related issues For open-access to the full report of this research, see below: