Culture is often treated as lists of context-general trait dimensions, such as power distance or individualism/collectivism. From this view, cultural awareness training often amounts to assessing dimensions for individual trainees, and showing how their responses differ from typical responses of the target culture. An important issue with this "dimensions" approach is that it can lead to a sophisticated form of stereotyping, as trainees learn overly simple models of the target culture. We have been exploring alternative conceptions of culture, as well as the processes by which experts, for whom successful cultural interactions are essential to their tasks, exploit opportunities to improve their cultural understanding. In the present paper, we describe a study in which participants with differing levels of expertise played the role of an Information Operations officer in a vignette. Specifically, participants (n=60) were either laypeople with no military background, novices who were trained in Information Operations, or individuals who had training and Information Operations field experience. The vignette was based a real incident set in Kosovo that was elicited by cognitive task analysis methods in an earlier study. The scenario contained surprising events associated with the respective target cultural group. Participants were asked to explain their understanding of the situation in a think-aloud procedure, as well as what they would want to know to inform their understanding. Our results indicated several differences between the strategies used by novices and experts to make sense of cultural anomalies. Experts tended to generate more alternative explanations than novices, were more likely to consider culture as an explanation for the surprising events, and tended to ask questions that would explicitly challenge fundamental assumptions underlying their conception of the culture. Implications of the study for cultural training are discussed.