Akrasia, or weakness of will, has been a significant philosophical problem since the time of Ancient Greek philosophy. Unfortunately, this topic has not been treated systematically in the phenomenological tradition. This paper seeks to redress this situation through a critical assessment of contemporary approaches to the problem of akrasia in light of a proposed phenomenological analysis. As this paper argues, a phenomenological approach over-comes an intellectualism often found in discussions of akrasia while identifying its distinctive kind of rationality. This paper further argues that there are no perfectly self-regulating agents and that weak-willed agents are able to vindicate their moral sanity.