Since the end of the Cold War, transatlantic partners have championed enlightenment principles and progressive values around the world, including gender equality. The extent to which the actors tasked with spreading these fundamental values also embody them within their own organizations – in this case within the diplomatic profession – is the focus of this research. This paper examines how women’s representation at the ambassadorial level has changed from 1990 to 2018 across the foreign services of the U.S., Germany, and the European Union (EU). A dataset constructed especially for this study compares: (1) the numbers of female ambassadors over time, (2) the ‘types’ of posts they are sent to, and (3) recruitment pipelines and training, including special characteristics like political appointments in the U.S. and different origins of EU ambassadors. The results show that the U.S. foreign service peaks at 40% women’s representation in 2017, the EU at 22% in 2014, and Germany only at 14.5% in 2018. Females disproportionately serve in small African nations, multilateral organizations, and former Soviet states. Female U.S. ambassadors are more likely to come from the career track, while political appointees are overwhelmingly male, at a ratio of 4:1. In Europe, two-thirds of female ambassadors previously worked at the European Commission and one-third in their national foreign service, while founding Member States – especially France, Germany, and Italy – are dominant. Interviews with seasoned diplomats help illuminate and contextualize the underlying causes that potentially drive these trends, including policy, historical, or cultural factors. Looking towards the future, this work provides a small, yet important building block in rooting the concept of gender equality firmly within the success strategy of each diplomatic corps. A future generation of foreign policy leaders depends on it.