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To explore the medical and surgical clinical dilemmas in the management of trans (transgender) men, a growing population receiving more attention than in the past.Testosterone therapy is commonly prescribed to trans men for masculinization. Nonetheless, the optimal formulations and doses of testosterone therapy for trans men have not been well established. Testosterone therapy has been associated with increased levels of hemoglobin and triglycerides, as well as diabetes. Periodic monitoring of hemoglobin, cholesterol, and fasting glucose is therefore recommended. As compared to non-transgender women, trans men have lower age-specific rates of breast cancer and cervical cancer which can be attributed, in part, to surgeries such as bilateral mastectomies and hysterectomies. The frequency in which to recommend mammograms and Pap smears (in patients with intact cervices) is uncertain in this population because of a lack of evidence-based data. Many trans men desire and undergo bilateral mastectomies with much fewer undergoing metoidioplasty or phalloplasty.For trans men, most clinicians target serum testosterone concentrations in the normal male reference range. The frequency of screening for breast and cervical cancer should be individualized based upon anatomy, patient age, age of initiation of testosterone therapy, and other factors.