The forensic assessment of transgender individuals is challenging because of evolving legal landscapes, sociopolitical tensions, gaps in the clinical literature, and lack of standardized assessments studied in this population. This article explores the complexities forensic psychiatrists encounter when evaluating transgender persons, with an emphasis on assessments of general and sexual violence risk, mitigating factors, sex discrimination, disability, emotional distress, and parenting. The article also addresses the importance of remaining vigilant in striving for objectivity in assessments of transgender individuals while acknowledging both the dearth of population-specific research and the vulnerabilities and risks faced by transgender individuals. Recommendations are made for ongoing research in this field.