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Abstract Objective The Headstrong program, a pharmacy based men’s mental health promotion program, was designed to enhance pharmacists’ care of men with mental illness and addictions and was focused on six conditions. A simulated patient (SP) encounter on insomnia was used to evaluate pharmacist’s performance as a part of the Headstrong program. Results Six Headstrong pharmacists consented to participate in the SP encounter as part of the evaluation of the Headstrong program. Pharmacists’ mean scores in most categories that were evaluated (e.g., pre-supply/assessment score, sleep score) were lower than expected. In assessing the SP during the encounter, pharmacists’ mean score was 5.7 (SD 2.0) of a possible 13 points. No pharmacists asked about the SP’s age, availability of other supports, allergies, and whether they had an existing relationship with a pharmacist. One pharmacist inquired about medical conditions, and two asked about pre-existing mental health conditions. Three pharmacists inquired about concurrent medications. The Headstrong program was discussed by half of the pharmacists and a resource recommended by the Headstrong program was suggested by one pharmacist. Several pharmacists used self-disclosure as a mechanism to support rapport building. Overall, the SP felt cared for and respected by the pharmacists and had confidence in their knowledge.