Many of us feel internally conflicted in the face of certain normative claims that make infeasible demands: say, normative claims that demand that agents do what, given deeply entrenched objectionable character traits, they cannot bring themselves to do. On the one hand, such claims may seem false on account of demanding the infeasible, and insisting otherwise may seem to amount to objectionable unworldliness – to chasing “pies in the sky.” On the other hand, such claims may seem true in spite of making infeasible demands, and insisting otherwise may seem to amount to treating the agents in question with undue lenience – to mistakenly letting them “off the hook.” What is going on? One possibility is that we are making a mistake. I explore the alternative hypothesis that our ambivalent reactions, far from involving any mistake, are entirely consistent and appropriate. Rather than some single privileged ought such that the idea that “ought” implies “feasible” is either true or false, there are simply different oughts that are supposed to be capable of operating in the service of, and playing distinct roles associated with, what I shall call different core normative practices. In particular, there is a) some salient core practice-serving ought for which it’s true that “ought” implies “feasible” and b) some other salient core practice-serving ought for which it’s false that “ought” implies “feasible.” I sketch a framework for understanding different core practice-serving oughts in general and then use this framework to consider which particular core practice-serving oughts might be capable of vindicating our ambivalence. I begin by considering and rejecting a prevalent and prima facie promising account according to which the relevant oughts are the prescriptive ought and the evaluative ought. I then propose a different account that holds that the oughts we need are instead the deliberative ought and the hypological ought.