The Liar sentence L, which reads ‘L is not true’, can be used to produce an apparently valid argument proving that L is not true and that L is true. There has been increasing recognition of the appeal of contextualist solutions to the Liar paradox. Contextualist accounts hold that some step in the reasoning induces a context shift that causes the apparently contradictory claims to occur at different contexts. Attempts at identifying the most promising contextualist account often rely on timing arguments, which seek to isolate a step at which the context cannot be claimed to have shifted or must have shifted. The literature contains a number of timing arguments that draw incompatible conclusions about the location of the context shift. I argue that no existing timing arguments succeed. An alternative strategy for assessing contextualist accounts evaluates the plausibility of their explanations of why the context shifts. However, even this strategy yields no clear verdict about which contextualist account is the most promising. I conclude that there are some grounds for optimism and for pessimism about the potential to adequately motivate contextualism.