This paper showed the results of a qualitative investigation that looked into intracultural communication between Brazilian teachers and students of English, and intercultural communication between American teachers and Brazilian students of English. The aims were to identify and describe contextualization cues used by both Brazilian and American speakers of English, and to connect these cues with sociocultural differences. Data was collected through footage of English classes in Brazil and through interviews with American English teachers. The analyses of the footage and the interviews have shown that, while assertiveness could be related to the sociological dimension of individualism in the American culture, compliance, as perceived in verbal interactions, could be connected with the collectivist orientation of the Brazilian culture. Moreover, the higher-context communication style in the Brazilian culture and the lower-context communication style in the American culture (when contrasted with each other) were found to be able to account for differences in the use of politeness strategies. The results showed the importance of making English students aware of contextualization conventions.