Imaginative resistance—i.e., the difficulty of engaging with certain fictional scenarios—is a phenomenon that has been explained in many different ways. A paradigmatic case is Walton's (1994) morally repugnant story: “In killing her baby, Giselda did the right thing; after all, it was a girl.” This paper develops a skill-based account of imaginative resistance. It argues that the phenomenon stems from the cognitive effort required to engage with scenarios that are distant from our experiences or habitual patterns of imagination. The greater this distance, the more likely resistance is to arise, even for competent imaginers. Beyond knowledge-that a given fictional world is such and such, I highlight the importance of knowledge-how to engage with said world. I then explain how this distinction constitutes a novel version of contextualism with respect to the phenomenon of imaginative resistance (compare Stock 2005, Todd 2009). A key strength of this account is its ability to explain how imaginative resistance can be shaped over time, allowing individuals to train their imagination to either embrace or resist various scenarios.