This thesis seeks to defend transitivity as a rational constraint on preferences against two putative counterexamples to transitivity. This thesis is divided into three sections. In the first section, I consider two famous and popular arguments in defense of transitivity and argue they are insufficient to adequately defend transitivity. I then outline a desiderata for successful arguments in defense of transitivity and identify some basic assumptions I will be making throughout the thesis. In section two, I consider the first putative counterexample to transitivity: Quinn’s Puzzle of the Self-Torturer. I offer two plausible interpretations of Quinn’s puzzle and argue that both fail. One because it does not genuinely induce intransitive preferences, and the other because the situation it requires is logically impossible. I conclude this section by defending my arguments against known objections in the literature. Finally, in the third section, I consider a counterexample to transitivity from Larry Temkin that has received little attention in the literature. I argue that while the initial counterexample is unpersuasive it can be augmented and made into a more forceful argument. I then argue that this improved counterexample fails due to some erroneous assumptions prevalent in the literature on incomparability. I conclude the thesis with a brief summary and some closing remarks.