Insurance coverage of gender-affirming surgeries including facial and vocal feminization surgery remains a challenge for many patients, physicians, and practice administrators. These challenges range from disparities in coverage for commercial versus public insurance carriers, in network versus out of network benefits, preauthorization struggles, and the lack of standard coverage policies. This article aims to describe the insurance coverage and approval challenges related to facial feminization surgery and to provide guidance for surgeons and their practice administrators on how to obtain successful preauthorization/predetermination, single case agreements, and proper claim adjudication.