Drug testing remains an area of discomfort and conflict for providers and patients particularly around the use of controlled substances. It takes months to years to build relationships with patients but only moments to destroy that relationship with accusations of unauthorized or illicit drug use. Modern drug testing is available in many forms and provides significant flexibility for providers, but interpretation remains a struggle for many providers. New immunoassay tests for fentanyl and other substances have introduced new complexities to treatment that are relevant to a provider’s practice and impact patient care now more than ever! Clinical practice guidelines and organizations such as the Centers for Disease Control (CDC) and American Society of Addiction Medicine (ASAM) endorse the use of urine drug tests (UDT) as a risk mitigation tool to assist clinicians with responsible prescribing of opioids. Unfortunately, clinicians often lack training in the use and interpretation of UDT results, which may result in consequential adverse outcomes for pain patients such as changes in treatment plan, removal of controlled substances, or the nonconsensual taper or discontinuation of controlled substances placing patients at further risk. This case-based interactive course will provide guidance to clinicians with understanding methods of testing, strategies to appropriately use and interpret UDT results including the utilization of a free novel software application to assist clinicians when facing unexpected results that yields illicit substances, false-positives/negatives, and guide when it is appropriate to consider quantifying results using definitive gas or liquid chromatography mass spectrometry. In addition to instruction on interpretation of results and further testing, this discussion will assist providers in navigating common pitfalls in navigating these discussions and demonstrate a proven approach to have these difficult conversations in a respectful and patient-centered approach.