We discuss the challenges of Web-based teaching for language teachers and then describe in detail an extended episode of misunderstanding that occurred between 2 students discussing their versions of history during a classroom-based, asynchronous telecollaborative project between learners of German in the United States and learners of English in Germany. We argue that discussion of such moments of miscommunication can be valuable learning opportunities for both students and teachers. They open up for explicit discussion what usually remains invisible in cross-cultural communication: the nature of the subject matter, the conditions of cross-linguistic exchanges, the nature of language as discourse, and the goals of foreign language education. Our analysis suggests that as students explore the nature of language and communication across cultures through their technology-mediated interactions, teachers are pivotal in helping them take an intercultural stance.