Fairy tale retellings have permeated literature, film, and media ever since the original stories emerged. New adaptations are constantly being released, and therefore new research must constantly be published. In this study, I analyze "Aschenputtel" by the Brothers Grimm, as well as various retellings of "Cinderella," including Andy Tennant's Ever After (1998), Mark Rosman's A Cinderella Story (2004), and Marissa Meyer's Cinder (2012). This selection includes a live-action historical film, a live-action contemporary film, and a science fiction novel, all with an intended audience of young adults. While the Brothers Grimm story and Ever After have already been analyzed in the context of gender representation (Zipes, Bottigheimer, Williams), prior academic research fails to adequately address the gender issues in A Cinderella Story and Cinder. Because Ever After, A Cinderella Story, and Cinder are more contemporary than the Grimms' "Aschenputtel," they are often thought to be more progressive (Gruner, Vera, Travers). However, I propose that they still have problematic implications, despite their publication in contemporary society. Jack Zipes, an acclaimed fairy tale scholar, argues that, "For the most part, the transformations [of contemporary Cinderella retellings] tend to be modern remakes with a faux feminist touch" ("The Triumph" 361). Similar to Zipes, I argue that, although the texts initially appear progressive and "feminist," they ultimately support problematic ideals related to gender. All three contemporary texts seem to ally themselves with an ethos of female empowerment through their protagonists' rejection of traditional femininity, but the inclusion of gender policing and the characters' eventual acceptance of hyperfemininity undermine this characterization, as does the ultimate heteronormative "happily ever after." Additionally, the use of competition (between Cinderella and her stepfamily, as well as new female characters) pits women against each other, often because of a man, which generally prevents the development of female camaraderie, other than with the fairy godmother. Further, rather than allying herself with female power (i.e. the mother), the protagonists in both Ever After and A Cinderella Story are defined by their relationship with the father, which minimizes their agency as it suggests a transfer of ownership from the father to the husband/prince. This framing of the protagonist by the father and prince (specifically as she works to "perfect" the prince) seems to relegate the female characters to a supplementary role, simply acting as a tool for the male characters' development.