On one way of understanding things, philosophical puzzles are divisible into three broad classes. The first class are easy to understand, but difficult to solve. The second class are difficult to understand, but coming to understand them places us far down the path of solving them. The third class are difficult to understand, and, even once understood, difficult to solve. The puzzle that this essay will be concerned with falls into the last of these classes. Tamar Gendler calls this puzzle the “puzzle of imaginative resistance.” This essay will be aimed at understanding the puzzle, and at making some progress towards solving it. The second of these aims will largely involve evaluating Gendler’s treatment of the puzzle, and attempting to draw some lessons from that evaluation. Gendler’s first and most direct treatment of the puzzle can be found in her essay, “The Puzzle of Imaginative Resistance.” That essay has three primary aims: i) to characterize the puzzle of imaginative resistance, ii) to argue that one natural solution to the puzzle is unsuccessful, and iii) to present her own solution to the puzzle. In what follows, I will be arguing that Gendler does not quite achieve her second and third aims.