The standard case of weakness of will involves a strong temptation leading us to reconsider or act against our judgments. Here, however, I consider cases of what I call ‘habitual weakness', where we resolve to do one thing yet do another not to satisfy any grand desire, but out of habit. After giving several examples, I suggest that habitual weakness has been under-discussed in the literature and explore why. These cases are worth highlighting for their ubiquity, and I show three (...) further advantages of appreciating habitual weakness as a kind of weakness: It challenges purportedly necessary conditions on akrasia, it side-steps outstanding skeptical concerns, and it provides a new model for considering the weak-willed behavior of group agents. I conclude by arguing that cases of habitual weakness are genuine cases of akrasia and weakness of will. Rather than lacking strength of will, habitual weakness involves lacking diligence, vigilance, or fortitude. (shrink)