In this paper I focus on the passage from the Critique of Practical Reason in which Kant refers to the experience of retrospective evaluation of one’s own immoral actions to confirm the validity of his claim that necessity and freedom can be attributed to the same action from different perspectives. Such experience is viewed both as awareness of being guilty and as repentance. I will first examine the complex context of moral self-assessment as it emerges through the awareness of guilt. I will then argue that Kant’s presentation of the moral emotion of repentance can lead to a deeper insight into his approach to self-assessment in its connection with moral responsibility. I will also show how the whole analysis can help to elucidate Kant’s commitment to the coexistence and compatibility of a causal and a teleological explanation as contrasting paradigms of description of an agent’s actions and existence. I will finally point to some problems raised by this thesis within the context of transcendental idealism.