If rationality imposes substantive constraints on belief formation, existing arguments for the connection between rationality and accuracy do not apply. In this paper, I assume that there are substantive constraints on rational belief and explore how we can bridge rationality and expected accuracy, given this assumption. In part I propose a prima facie plausible answer to the "bridging question" and show that it can do important explanatory work. In part II, I argue that higher order evidence considerations pose a serious problem for the claims and arguments I developed in part I. I then propose an alternative answer to the bridging question that accommodates and explains conciliatory views about higher order evidence. The alternative answer appeals to the idea that the principles of rationality aren't the ones that are the best to follow – they are the ones that are the best to try to follow. However, if a theory of rationality satisfies the trying account, it won't be able to play all of the roles we may have hoped it would. I conclude with the thought that there are two important notions of rationality, each corresponding to a different way in which we care about accuracy.