England’s education system has a long history of boarding schools, with upwards of 75,000 boarders educated each year (Boarding Schools Association, 2020a; Independent Schools Council, 2020). Boarding schools are regarded as unique educational environments and, in recent times, there has been increasing consideration of the value and effect of these environments on the wellbeing of both staff and students. To date, proponents and opponents of boarding education have been unable to resolve their differing perspectives on the impacts of a boarding education on staff and student wellbeing. This uncertainty has occurred in the context of increasing rates of teacher attrition alongside the expanding role schools are expected to play in the domain of student personal development. Despite existing research documenting the importance of organisational factors as determinants of wellbeing, such as staffing factors, the focus often remains on the individual, with little research specifically addressing the boarding environment itself. In the context of this research need, this exploratory qualitative study compared the impact of two emergent boarding school staffing models on staff and student wellbeing through the perceptions of boarding school staff. A comparative case study methodology was employed, with purposive selection of two schools in England as instrumental case studies representing each of the two emergent models: a) the teacher-led model, which favoured the use of teaching staff in dual teaching-boarding positions, and b) the distinct-staff model, which favoured separation between boarding house staff and teaching staff. Data were collected through a document analysis of school-based policies and webpages and external inspection reports, together with semi-structured interviews with five boarding house staff at each site. The lived experience of boarding school staff was privileged within this study through the application of standpoint theory (Allen, 2017) and a relational wellbeing framework (S. White, 2010, 2017) used for the identification of broad determinant factors. Data analysis was conducted using Leximancer (Smith, 2016), an automated data mining software package, and complemented with line-by-line manual processes. Document analysis utilising Leximancer revealed that the case study contexts were comparable with respect to their policy environments and school-based factors, with differences predominantly emerging from the staffing model in use. Analysis of interview data utilising Leximancer revealed five key themes: Boarding, School, Children, Time, and Work. These themes reflected a textual focus on contextual factors, with substantial similarity emerging between the two case study sites with respect to the ranked concepts identified. This contextual focus and resulting similarity highlighted a common lived experience of participants between case study sites and provided a foundation for manual analysis of the interview data. Manual line-by-line analysis identified five themes through which staff and student wellbeing was framed in relational terms: Provision, Roles, Routines, Relationships, and Fit. Responsive to both the interview data and factors identified in the literature, these themes were united with the contextual themes which emerged from Leximancer analysis to produce a conceptual framework for the study. This conceptual framework supported the development of differences between the two models with respect to the composition of staff roles and their impact on role stress and role conflict and the consistency of boarding routines with respect to continuity of care. Patterns of boarding provision, quality of relationships, and reciprocal person-organisation fit were interrelated and important in both cases but were secondary to Roles and Provision as differentiating factors. The models were deemed to be justifiable constructions based on study observations. Findings from this small-scale study recommend the distinct-staff model as most supportive of staff and student wellbeing. This study found that the separation of teaching and boarding roles served to reduce role stress and role conflict for boarding and teaching staff alike, producing benefits for both staff and student wellbeing in this research context. Participants in the distinct-staff case reported that this model provided improved continuity of care to boarders through greater consistency in the staffing of the boarding house. Additional implications and guiding principles for schools to support the wellbeing of staff and students in boarding included: (a) adapt provision responsively to reflect the needs of current staff and students; (b) evaluate staff roles to minimise role stress and role conflict; (c) review routines and transitions to facilitate continuity of care; (d) support relationship development both professionally and personally; and (e) maximise fit between individual needs and the requirements of the institution. Exploratory in nature, this study has contributed to the limited boarding school literature base, providing the foundation for future research needed to generalise these findings more confidently.