In the 1990s, Dr. Toby Meltzer was an Assistant Professor of Plastic and Reconstructive Surgery at OHSU and the Chief of the Division of Plastic and Reconstructive Surgery at the Veterans Administration. He began practicing at OHSU in 1990 and began private practice in Portland in 1996. At the time, he was one of the youngest in his career and today is considered a pioneer in surgical techniques for gender affirming genital reconstructive surgeries and one of the leading surgeons in the field. This interview discusses his early career and the limits and obstacles of information and training in transgender healthcare for providers as well as the challenges to providing transgender healthcare in the nineties, and how these challenges have evolved and progressed. Dr. Meltzer discusses the moving of his practice from Oregon to Arizona, and issues such as insurance benefits accessibility for transgender patients, the influence of the Human Rights Campaign, opinions on the effectiveness of sensitivity training, legal challenges, and his perspectives on the past and present state of resources and training for gender affirming genital surgeries.