Risk assessment and stratification have become important aspects for the prescription of opioids to patients with chronic pain. Recent research has shown that the Opioid Risk Tool (ORT), a widely used risk assessment tool, has poor predictive abilities when compared with other risk assessment methods. This study compares two different methods of administration of the ORT to further study this issue. Patients at a pain practice were given an ORT to complete per the usual method of administration. In addition, a separate blinded ORT was completed by a psychologist after conducting a clinical interview with the patient. The results of the patient-completed ORT (PC-ORT) and the clinician-completed ORT (CC-ORT) were compared. There were significant differences found between the two, with the psychologist usually rating the patient higher in risk. The CC-ORT demonstrated better prediction of aberrant drug-taking behavior than the PC-ORT. The items that were discrepant between the two suggest that the differences were primarily due to comprehension issues. A strategy to help maximize the usefulness of the ORT derived from this finding and clinical experience is discussed.