Transgender student rights have been a controversial topic in schools across the country in recent years. The Arcadia Unified School District was one of the first districts in the country to have a complaint filed against it and to reach a settlement agreement with the U.S. Department of Justice. Through this years-long journey, the Arcadia Unified School District learned from its mistakes, learning how to better work with and advocate for transgender students. After a plethora of negative stories about this issue, the willingness for Arcadia to break its public silence and open up to the media led to Superintendent Dr. David Vannasdall being featured on ABC 20/20 with Diane Sawyer. We discuss the journey as well as the detailed process and preparation for this national tv event.