Dynamic interplays of identity circulate within any form of supervision. When supervisors and students also originate from diverse cultures, these complex forces become overlaid with additional cultural factors that must be taken into account in supervision pedagogy. Previous colonial discourses, stereotypes, and histories may surface in challenging and perplexing ways. This paper explores the supervision experiences of some culturally diverse supervisors and students in Engineering at an Australian university, who were part of a larger study. I investigate how supervisors demonstrate their transcultural knowledge by offering students choices in the ways they supervise them. I also investigate moments when students may be forced to assimilate to Anglo-Australian knowledge. There are also ambivalent moments when the differences between helpfulness and paternalism become blurry and when cultural difference interplays in surprising ways with personal experiences. Preliminary explorations of the implications these analyses have for intercultural supervision pedagogy are outlined.