It has long bothered readers of Kant's Groundwork that Kant takes himself to be reconstructing ordinary morality and yet assigns no clear place to the emotions that support morality. Indeed, in the Groundwork, emotions often seem to be either enemies of morality or immediate and impulsive inclinations that have no reliable or noteworthy connection to moral practice. Though on a friendly reading of the first chapter of the Groundwork the assignment of moral worth for the performance of a dutiful action does not entail that emotions cannot be present, that same reading still leaves it unclear what substantive role emotions might have in a Kantian account of moral conduct. The worry is somewhat alleviated by the time we come to the later works. There Kant recognizes the duty to develop emotions as a part of our duties of virtue. We have a duty to habituate empirical character, including our passional natures. Our agency extends deeply to the cultivation of emotions. More specifically, according to The Doctrine of Virtue, our end-setting capacities (i.e., rational agency) are sustained and developed by the setting of obligatory ends and sub-ends. These require the cultivation of our natural powers and receptivities in ways that empower our agency. Included among these receptivities are emotions. Yet positing a duty to cultivate emotions as part of a general project of moral development again leaves open the question of what roles these emotions will play within a conception of moral character ultimately grounded in reason. In this essay I want to explore this issue in the context of revisiting some of Kant's texts.