This study focuses on the gendered nature of ambassadorial appointments. Analyzing the diplomatic services of ten Latin American countries between 2000 and 2018, we examine the factors that explain the designation of women to ambassadorships. More especially, we are interested in whether the election of women to the presidency in Argentina, Brazil, Chile, and Costa Rica had an impact on the gender gap at the top of those countries' foreign services. Drawing on an original dataset on diplomatic appointments, we show that the presence of women ambassadors has increased only marginally over the past two decades. Furthermore, multivariate regression analysis demonstrates that women presidents on the left have (partially and temporarily) corrected the gender gap in their foreign services through political appointments, provided they had the discretionary powers to do so. Our findings suggest that the impact of women-led presidencies is conditional on the chief executive's vested interest in gender parity and the scope of presidents' prerogatives to appoint ambassadors. In so doing, the study contributes to debates on the descriptive underrepresentation of women in executive positions and the gender gap in diplomacy.