Kant’s conception of remorse has received little discussion in the literature. I argue that he thinks we ought to experience remorse for both retributivist and forward-looking reasons. This account casts helpful light on his ideas of conversion and the descent into the hell of self-cognition. But while he prescribes a heartbreakingly painful experience of remorse, he acknowledges that excess remorse can threaten rational agency through distraction and suicide, and this raises questions about whether actual human beings ought to cultivate their consciences in such a way as to experience remorse in the way he conceives it.

Kant’s account of the pain of remorse involves a hybrid justification based on self-retribution, but constrained by forward-looking principles which say we must channel remorse into improvement and moderate its pain to avoid damaging our rational agency. Kant’s corpus also offers material for a revisionist but textually grounded alternative account based on wrongdoers’ sympathy for the pain they cause. This account is based on the value of care, and has forward-looking constraints much like Kant’s own account. Drawing on Kant’s texts and recent work in empirical psychology, I argue that sympathetic remorse may fulfil Kant’s forward-looking goals better than self-retributive remorse.

Kant’s theory of friendship is crucial in defending his ethics against the longstanding charge of emotional detachment. But his theory of friendship is vulnerable to this charge too: the Kantian sage can appear to reject sympathetic suffering when she cannot help a suffering friend. I argue that Kant is committed to the view that both sages and ordinary people must suffer in sympathy with friends even when they cannot help, because sympathy is necessary to fulfill the imperfect duty to adopt others’ merely permissible ends (MPEs), and we ought to take friends’ MPEs as our own. MPEs are individuated in terms of concepts which include marks of the first person, and no marks of law other than permissibility. To adopt ends of others individuated in terms of such concepts rather than merely promote them as means to different ends, those concepts must engage with one’s feelings in a way that requires sympathy.

This paper argues that Kant endorses a distinction between rational and natural sympathy, and it presents an interpretation of rational sympathy as a power of voluntary a posteriori productive imagination. In rational sympathy we draw on the imagination’s voluntary powers (a) to subjectively unify the contents of intuition, in order to imaginatively put ourselves in others’ places, and (b) to associate imagined intuitional contents with the concepts others use to convey their feelings, in such a way that those contents prompt feelings in us that are like their feelings.

In contemporary free will theory, a significant number of philosophers are once again taking seriously the possibility that human beings do not have free will, and are therefore not morally responsible for their actions. (Free will is understood here as whatever satisfies the control condition of moral responsibility.) Free will theorists commonly assume that giving up the belief that human beings are morally responsible implies giving up all our beliefs about desert. But the consequences of giving up the belief that we are morally responsible are not quite this dramatic. Giving up the belief that we are morally responsible undermines many, and perhaps most, of the desert claims we are pretheoretically inclined to accept. But it does not undermine desert claims based on the sheer fact of personhood. Even in the absence of belief in moral responsibility, personhood-based desert claims require us to respect persons and their rights. So personhood-based desert claims can provide a substantial role for desert in free will skeptics’ ethical theories.