AbstractRecent literature on Stalnaker's Thesis, which seeks to vindicate it from Lewis (1976)'s triviality results, has featured linguistic data that is prima facie incompatible with Conditionalization in iterated cases (McGee 1989, 2000; Kaufmann 2015; Khoo & Santorio, 2018). In a recent paper (2021), Goldstein & Santorio make a bold claim: they hold that these departures light the way to a new, non‐conditionalizing theory of rational update.Here, I consider whether this new form of update is subject to a Dutch book. On the official, invariantist version of the theory, I show that the answer is “yes”. On a competing, contextualist theory of indicative conditionals (Bacon, 2015), the answer is “no”, for reasons that have familiar connections to the limits of textbook Bayesianism. After presenting a concrete case, I explore the dialectical ramifications. The upshot is some hard choices for theories that seek to save the linguistic phenomena.