This paper investigates the experiences of Western teacher expatriates in a Shanghai international schooling organization. We explore the risks and benefits associated with transnational mobility and how teacher expatriates, as part of the global middle-class (GMC), maintain and reaffirm their middle-class status. Focusing on adaptation and constraint in professional contexts, the data illustrates how the teachers respond to new discourses and the rules of exchange in the rapidly changing Chinese education market. We operationalise transnational habitus, as a conceptual tool, to explore how certain identities are sustained and negotiated in various moments of unsettlement. As these teacher expatriates navigate new professional contexts, we see how their habitus remains heavily influenced by class and previous professional experiences in their country of origin as they engage in new work environments, in order to secure an advantageous position.