Many remote Aboriginal Australian students live away from home for periods of time to access secondary education through boarding schools. While financial, political and community support is burgeoning for boarding models that provide scholarships, sports programs, or accommodation for Aboriginal and Torres Strait Islander students, very little academic research or evidence exists that examines the experiences of students post-boarding. This paper forms part of a broader doctoral research study and specifically focuses on how past students, families and communities from remote South Australia view the outcomes of boarding. Using a grounded theory design, thematic analysis of 32 semi-structured interviews with past students, families and community members led to the identification of three main themes: connections (early exits), community (re-engaging in education), and context (employment in remote communities). Findings indicated that outcomes are not linear, nor easily defined. Developing a theory of change was recommended as a future approach to help families, students and remote schools to clearly define goals and measures of success for each student, recognising a range of interpretations and conceptions of "success", and adapting these goals as necessary.