This article situates secondary schooling within the evolving transnational social field. Drawing on 43 interviews with teachers and former students with transnational connections in the Greater Toronto Area (GTA), Canada, I examine how transnational practices and dispositions fit within existing curricular and pedagogical frameworks in secondary schools. It is suggested that the 'ways of being' and 'ways of belonging' for transnational students are in conflict with the teachers' views on how students ought to act and feel within classroom settings. When transnational secondary students travel to their sending societies for ongoing periods, the data reveal disconnections at school that threaten the dominant classroom norms. When there is sustained direct contact with multiple countries, including both travel and new modes of communication, this may create knowledge and vivid experiences for transnational youth who are 'betwixt and between', but also leads to concerns by teachers about a 'strategic' use of Toronto-area schools and fears about 'dual loyalties'. Finally, many of the transnational youth find their teachers' assumptions of schooling superiority in the Global North to be sorely misdirected, and perhaps even harmful. These discordances highlight the existence of competing systems of capital within GTA classrooms.