|This dissertation serves to support deliberate attempts to cultivate moral character. Character education faces criticism, some of which are inherited from its grounding in virtue theory. The aim of this dissertation is to confront these particular critiques and show that they can be answered in an effort to vindicate the prospects of character education. When philosophers question whether character traits are stable and robust in the way that virtue theory posits them to be, a similar problem holds for character education: is there any point to character education if character does not exist in the way we traditionally think about it? I appropriate Christian Miller’s Mixed Traits framework to show that character education can handle standard situationist challenges that maintain that our environments are better predictors of our behaviors than our characters. Another problem concerns the possibility of developing the kinds of character traits that character education dictates. I defend the possibility, motivated in part by the work of Michael Slote, Nancy Snow, and others. I argue that active cultivation is not only the most promising method for character development, it is also necessary for becoming virtuous. I defend a two-tier approach to character and virtue acquisition that is skill-based, and involves teaching and fostering skills of self-awareness, perception, and responsiveness. My account faces opposition on grounds that various influences can interfere in the process of cultivation. Eric Schwitzgebel and Jennifer Saul raise skepticism regarding the extent to which we can rely on our mental faculties, and Heather Battaly challenges the role environment can play in virtue development. I recognize the call for strategies to overcome both internal and external influences and respond by drawing on contemporary empirical research. Teaching skills of self-awareness, perception, and responsiveness, and offering opportunities to practice these skills will enable students to become virtuous. This project is grounded in and motivated by philosophical, psychological, and educational research. It proposes a realistic and empirically supported approach to character development. I am optimistic that a skill-based approach will enable students to become virtuous, and hopeful that it will be implemented in curriculum in the future.