Sport officials are tasked with making quick and accurate decisions, maintaining order, communicating with athletes and coaches, and enhancing athletes’ safety. In most sports, more male than female sport officials are recruited and retained. The limited research focusing on female sport officials suggests that their experiences are frequently negative. Further understanding female sport officials’ experiences is imperative for learning more about their intentions to begin and continue (rather than quit) as officials. The purpose of this study was to explore the positive and negative experiences of female sport officials who operated in sports where the officials were primarily male. Nine sport officials participated in semi-structured interviews. Thematic analysis was used to identify and code common themes within the data, many of which aligned with the principles of Self-Determination Theory. The main themes discussed herein are (a) The Female Experience (pertaining to the context and environment in which they operated), (b) Facilitators (influences that assist with the responsibility of officiating), and (c) Barriers (circumstances or regulations that have had negative impacts on advancement and development). These themes highlight the inequality females are confronted with in the sport officiating environment, but they also provide helpful tools to promote a more positive environment. By using these tools, female sport officials are more likely to continue and thrive as officials, rather than resign. Recommendations will be provided for sport governing bodies, officiating organizations, and sport officials, which might contribute to future policy changes that lead to increased recruitment and retention of female sport officials.