As business schools internationalise and attract students from multiple locations, we witness growth in innovative business curriculum that enables students and staff to engage and act globally. Management of learning and teaching in the transnational business education program can be a true challenge for institutions in both home and host countries, especially with leadership and governance. In this paper, we seek to define challenges in engaging business students in a transnational education program operating in Singapore and Australia. From the interviews with students and staff, we identify feedback, communication, and transferability as important factors promoting engagement among students in the transnational program. We highlight learning strategies to support ongoing engagement among students in the transnational business education program. It is confirmed in this paper that contextualising the local and international context is crucial in the management of transnational business education program if students are to develop cross-cultural competencies.