As cross-cultural interactions become more commonplace and of shorter durations, understanding the abilities that enable some sojourners to function competently in unfamiliar cultural contexts is increasingly important. The present investigation took a cognitive science approach to the problem of cross-cultural competence, examining metacognitive strategies for dealing with puzzling interactions. A think-aloud study of cross-cultural expertise was conducted using two scenarios based on real incidents set in two different cultures. Each scenario contained surprising cultural behaviors. Three groups of participants (n = 60) with varying levels of expertise were compared. The results indicated several differences in the metacognitive strategies used to make sense of cultural anomalies. Overall, the types of reasoning cross-cultural experts engage in to make sense of cultural surprises were found to share characteristics with the reasoning processes exhibited by expert scientists. The findings of the current study have several implications for training specific aspects of cross-cultural competence.