This paper explores the case of US President George W. Bush’s unwavering support for the Republic of Georgia in its aggressive engagement with Russia during the 2008 August War, a nearly universally acknowledged judgment error that puzzled Bush’s own team as much as it did foreign policy analysts. Finding explanations grounded in alliance behavior, audience costs, and resource security inadequate, the paper offers a cognitive heuristics account that focuses on the fundamental attribution error (FAE). Examining how the FAE can function in terms of assessing the actions of perceived friends reveals Bush’s failure to update his beliefs about the increasingly erratic behavior of Georgian President and Bush confidante Mikhail Saakashvili. In presenting an explanation for this empirical puzzle, the paper contributes a new perspective on the FAE of use in the burgeoning literature employing psychological approaches to foreign policy outcomes.