Scholars have interpreted the feminist quality of Ana Caro’s Valor, agravio y mujer , and its protagonist Leonor, through various paradigms, as part of what Robert Bayliss terms “the post- dramaturga era.” Many interpretations of Caro’s play, however, ignore an essential element of Leonor’s plot as the avenging mujer varonil so as to reconcile her essentially deviant cross-dressing, skillful manipulations, and courage with the conventional marriage at the end of the work, interpreting the marriage arrangement as Leonor’s desired conclusion, or goal. This study aims to underscore Leonor’s wish to murder, and not marry, Don Juan, and the way in which this violent intention reveals her innovative position that eludes the female/male dichotomy. Given that she has shifted the female/male divide, Leonor can use tools from one side of her identity to remedy the other. In an episode of the memoir of another crossdressed figure of the time, Catalina de Erauso, violence as a masculine device works against masculine advantage, similarly highlighting woman’s disadvantaged position as related to the honor code. By comparing the two figures, we may better comprehend an overall discursive imagination of female cross-dressing in seventeenth-century Spain and reconsider the nature of Leonor’s plight in Caro’s play.