Introduction: School-level student support programmes provide students with pastoral care and support for academic, wellbeing and other issues often via a personal tutor (PT). PT work is a balancing act between respecting the confidential information divulged by students and doing what is expected in terms of accountability and duty of care. We aimed to explore how tutors manage this tension, with the aim of advancing understanding of student support programmes. Methods: This qualitative study was informed by an Institutional Ethnography approach. We conducted 11 semi-structured interviews with PTs from one medical school in Singapore. We considered how they worked in relation to relevant national and institutional-level policy documents and reporting guidelines. Data collection and analysis were iterative. Results: We crafted two composite accounts to illustrate the dilemmas faced by PTs. The first depicts a PT who supports student confidentiality in the same way as doctor-patient confidentiality. The second account is a PT who adopted a more mentoring approach. Both tutors faced confidentiality challenges, using different strategies to “work around” and balance tensions between accountability and maintaining trust. PTs were torn between school and student expectations. Discussion: Fostering trust in the tutor-student relationship is a priority for tutors but tensions between confidentiality, accountability and governance sometimes make it difficult for tutors to reconcile with doing what they think is best for the student. A more nuanced understanding of the concept of confidentiality may help support PTs and ultimately students.