Access to secondary education for very remote Northern Territory Aboriginal students is limited. Although many students attend distant boarding schools, very few stay to complete Year 12. Few families and communities are fully engaged in the whole transition process. However, one very remote Aboriginal community has partnered with an interstate urban boarding College resulting in Aboriginal students staying to complete Year 12 and seeking local employment pathways afterward. This study investigates how the elements within this partnership works by asking three questions: 1) How do two diverse communities communicate with each other?; 2) How does a boarding College both maximise educational opportunities whilst keeping students culturally safe? and; 3) How do both communities learn from each other? Seeking answers to these questions, using a qualitative methodology with a phenomenological design, two adults from the remote Aboriginal Community and six staff from a partner boarding College were interviewed. Interviews were transcribed verbatim, thematically coded and deidentified. Findings were summarised into thematic clusters: (1) Communication; (2) Relationships;(3) Student Factors; (4) Learning; (5) Language and Culture; (6) Collaboration. Themes were also coded using a Bronfenbrenner Ecological framework to identify how two diverse communities work together within different layers of the partnership. Some key points include values of trust, cultural understanding and intentional vision within the Macrosystem; both-ways learning within the Exosystem; reciprocal relationship links within the Mesosystemand peer-peer relationships in the Microsystem. Implications include sustainability maintenance in the Chronosystemby developing reciprocal community visits, student opportunity in ‘both worlds’ and deepening cultural knowledge through learning exchanges. Limitations included small sample size not completely representative of the students, families, Elders and staff from both communities. This research offers a rare example of student achievement and the possibility to replicate some parts of this model with others on a similar journey.