On an account of virtue as skill, virtues are acquired in the ways that skills are acquired. In this paper I focus on one implication of that account that is deserving of greater attention, which is that becoming more skillful requires learning from one’s failures, but that turns out to be especially challenging when dealing with moral failures. In skill acquisition, skills are improved by deliberate practice, where you strive to correct past mistakes and learn how to overcome your current limitations. A similar story applies to virtue acquisition, as moral failures will be a part of anyone’s life, and we will all have to learn from these experiences. However, despite the importance of being able to learn from our mistakes, this is very difficult in practice, given that failure of any kind can be distressing, and especially so for moral failure. The distress created by a recognition of moral failure often prompts responses of anger, avoidance, or defensiveness; rather than attempts to make amends and when necessary to work on self-improvement. The most potentially distressing response to moral failure is shame, as it is often associated with defensiveness. It is here where emotion regulation will be important to manage that distress, and I focus on the skill of emotion differentiation. I argue that emotion differentiation is a promising strategy for distinguishing the emotions we may experience in the wake of failure, including shame, and to encourage those emotions that motivate self-improvement. Thus, emotion regulation is important for virtue acquisition.