The understanding of concepts like moral distress and countertransference in mental health settings has advanced over time. While organizational constraints and the clinician's moral values are conventionally thought to play a part in evoking such responses, certain behavioral transgressions might be universally deemed as morally unacceptable. The authors present case scenarios that took place during forensic assessments and routine clinical care. Clinical interactions evoked a diverse range of negative emotional reactions, including anger, disgust, and frustration. The clinicians struggled with moral distress and negative countertransference, which resulted in difficulty mobilizing empathy. Such responses could affect a clinician's ability to best work with the individual and could even affect the clinician's well-being adversely. The authors put forth several suggestions on how to manage one's own negative emotional reactions in similar settings.