Sex and gender are increasingly complex topics that prompt new policy and administrative responses within public agencies. As the federal workforce evolves, federal employment policy must accommodate the needs of employees who do not fit traditional sex/gender categories. One emerging area of policy targets transgender employees, particularly policy that guides the employer response throughout the transitioning process. This research seeks to answer the following questions: How can transitioning policy and implementation within federal agencies affect employees? and How should transitioning policy be crafted and implemented? This work addresses organizational behavior and management issues by presenting a successful case of a workplace transition. Interviews of an administrator guiding the transitioning process and one of the first federal employees to complete a transition while in a federal field office are conducted. Ultimately, this research explores challenges with emergent policy and suggests avenues for designing and enacting future transitioning policy.