This chapter is a reflection upon the challenges – practical, cultural and epistemological – of supervising graduate theses in Literary Studies in the School of Language, Arts and Media at the University of the South Pacific. It does not attempt to recap the mostly sound principles provided in general guides to effective graduate supervision. Instead, it focuses on two key aspects that are underrepresented in the scholarship generally, and almost completely undiscussed in the Pacific Island context: graduate diversity and the cultural challenges introduced by the use of supervisors from outside of the region. Proceeding from the understanding that the experiences of graduates in the Pacific Islands are not adequately represented in educational research, the chapter utilises a mixed method, though primarily qualitative, research methodology. It draws upon Pacific-led research on educational practices in the Pacific Islands, makes comparisons with the neighbouring (but not identical) context of Māori supervision in Aotearoa/New Zealand, refers to University data around enrolment and retention, and presents the findings of a survey conducted with research graduates, enrolled in Literature research Master’s or PhD programmes at the University of the South Pacific in the past decade.