In this article, we examine the gendered outcomes of career negotiations, which involve employees discussing career advancements with their direct supervisors. We apply relational inequality theory, which conceptualizes career negotiations as instances of relational claims-making, to explain gender differences in returns in terms of hourly wages, occupational status, and subjective perceptions of job advancements. Our empirical approach employs individual fixed-effect models using three waves of unique German linked employer-employee panel data on 2090 employees across 131 workplaces (LEEP-B3; 2012–2019). We find that men discussing career advancements with supervisors, experience pay raises and occupational upward mobility, whereas women do not. Yet, we find only minor gender differences in perceived job advancements following career negotiations. In workplaces with a more balanced gender representation in management and supervisory positions, women’s wage returns from negotiations increase. Although individual negotiations seem to perpetuate gender inequalities, workplace structures can weaken inequality-generating mechanisms.