This paper focuses on a single question that highlights some of the most puzzling aspects of Kant’s explanation of the duty of moral self-perfection. What kinds of activity count as striving for purity in one’s disposition to duty, or strength of will? I argue that a dominant strand of Kant’s approach to moral striving does not fit familiar models of striving. I seek to address this problem in a way that avoids the flaws of synchronic and atomistic approaches to moral self-discipline by developing an account of Kantian moral striving as an ongoing contemplative activity complexly engaged with multiple forms of self-knowledge.