Prescribing medications to patients with cooccurring psychiatric and substance use disorders often evokes distressing emotional responses from both clinician and patient that affect the delivery of appropriate pharmacological treatment. One important polarization revolves around the clinician under-prescribing to avoid feeling like he or she is overmedicating the patient versus over-prescribing when risk levels are minimized. A case report illustrates some common, rapidly shifting responses to both medication and clinician. These reactions include 1) an idealized, passive relation to the medication followed by disappointment in its weakness, 2) minimizing the danger of medication through idiosyncratic and potentially dangerous overuse to replicate effects of the addictive substance, or 3) experiencing the medication as harmful, leading to phobic avoidance and underutilization. The recommended clinical response is to avoid these polarizations and to engage with the patient's suffering and dangerous behavior by 1) taking reasonable pharmacological risks, 2) establishing provisions for safe use and frequent monitoring, 3) conveying tolerance for idiosyncratic use within safe limits, 4) regular exploration of the meaning of the medication with links to both the addiction history and the treatment relationship, and 5) frequent psychoeducation.