Increasingly, remote Aboriginal families are being encouraged to transition their children into boarding environments to complete secondary schooling. This comes largely from recent policy recommendations and implementation of a strategic plan to redistribute funding and resources away from secondary education provision in remote and very remote communities in the Northern Territory. Although some suggest that boarding environments are contributing to improved educational outcomes for Aboriginal and Torres Strait Islander students across Australia, others have cautioned the need to address the complex considerations that families, boarders, and boarding environments encounter before, during and beyond boarding. With limited data currently available, analysed, or reported on, we propose that careful consideration and understanding of the frontline experiences of boarding providers, families, and past boarders will provide a more solid grounding for current and future policy decisions. This paper presents data from a broader doctoral research project examining each of these, however specifically aims to highlight the experiences of families of boarding students, and their integral role in the boarding process. Encouragingly, increasing awareness and care is being taken by boarding providers to understand parents’ experiences and to guide and support them if necessary. However, to date, limited research presents the perspectives of remote Aboriginal families. Employing a Grounded Theory approach, this project used qualitative semi-structured interviews conducted with 11 participants (parents, caregivers or family members of students in a residential program) from the remote South Australian Anangu Pitjantjatjara Yankunytjatjara (APY) lands. Thematic analysis is currently being conducted on this data, however initial findings suggest three key insights. Firstly, the decision to board was not always the parents’ decision, often coming from the students themselves or as a suggestion by community teachers. Secondly, families often navigate between different boarding providers depending on the child, the situation, or their knowledge and trust in particular programs. Finally, support and guidance from parents and family were found to be integral to the outcomes of students who had returned home prematurely (i.e. prior to finishing schooling). This research provides valuable a valuable contribution to the field with stories from families who have and continue to engage with boarding providers. The implications of this research are useful not only to boarding providers but to education departments and policy makers alike as they consider how best to support and engage meaningfully with remote families and communities transitioning in and out of boarding.