While it is well understood that the content included in an apology matters, what constitutes an effective apology may differ depending on the gender of the person delivering it. In this article, we test competing theoretical perspectives (i.e., role congruity theory and expectancy violation theory [EVT]) about the relative effectiveness of apologies that include language that conforms (or not) with the gender stereotypes ascribed to the apologizer. Results of four studies supported an EVT perspective and showed that apologies were perceived to be relatively more effective when they contradicted gender stereotypes (i.e., communal [agentic] apologies by men [women]). Specifically, Study 1 provided an initial test of the competing hypotheses using celebrity apologies on Twitter. Then, results of three experiments (Studies 2, 3a, and 3b) built upon these initial findings and tested the psychological mechanisms proposed by EVT to explain why counterstereotypical apologies are beneficial (i.e., attributions of interpersonal sensitivity [assertiveness] and enhanced perceptions of benevolence [competence] for men [women]). Our contributions to theory and practice are discussed.