Background <p>Laparoscopic hysterectomy is a core component of gender-affirming care for transgender men. However, long-term testosterone therapy can lead to anatomical and tissue changes that increase the complexity of pelvic surgery.</p> Objective <p>To describe the intraoperative complications encountered during gender-affirming laparoscopic hysterectomy in transgender men receiving testosterone therapy and discuss strategies for mitigation.</p> Methods <p>This retrospective case series includes four transgender men undergoing total laparoscopic hysterectomy at a tertiary academic center. All patients were nulliparous virgins with ≥ 2.5 years of testosterone therapy. Clinical data, intraoperative events, and management strategies were analyzed.</p> Results <p>Intraoperative complications included posterior cul-de-sac perforation (<i>n</i> = 1), cervical avulsion requiring conversion to laparotomy (<i>n</i> = 1), bladder dome injury (<i>n</i> = 1), and deep vaginal lacerations (<i>n</i> = 4). Contributing factors were cervical atrophy, stenosis, and limited vaginal elasticity due to long-term testosterone exposure. Multidisciplinary support was required in two cases (urology and vascular surgery). All patients recovered without long-term sequelae, although one expressed dissatisfaction with abdominal scarring.</p> Conclusion <p>Gender-affirming hysterectomy in transgender men presents unique challenges related to testosterone-induced anatomic changes. Preoperative planning, gentle tissue handling, customized instrumentation, and patient counseling are critical to reduce risk and optimize outcomes.</p>