This three-paper dissertation explores challenges to moral transformation and moral development. The first two papers explore puzzles that challenge whether moral transformation is possible in the way it is usually conceived. In the first paper, I address the issue of whether it is possible to rationally choose to morally transform. Recently, Laurie Paul has argued that it is impossible to rationally choose to have what she calls a transformative experience. I argue that moral transformation is a species of transformative experience and also, against Paul, that it is possible to rationally choose to morally transform. In the second paper, I address a challenge to the process of moral development. According to Aristotle and others, one becomes virtuous by acting as the virtuous person acts. But how is this possible if one is not already virtuous? I argue that it is, but one must first practice habituating the practical attitudes (i.e. the beliefs and desire) of the virtuous person. In this way the self-controlled person and the weak-willed (or akratic) person can grow in virtue. Additionally, I provide practical exercises—types of spiritual disciplines and moral drills—to help learners shape their practical attitudes. In the final paper, I explore an instance where moral development is disrupted. More specifically I show how moral injury interrupts and causes dysfunction within one’s character, making further transformation towards virtue impossible. I then identify strategies and tactics to inoculate people, especially soldiers, from moral injury—what I call developing the virtue of moral resilience—thereby safeguarding their path to moral development.