This research investigates the self-reported perceptions, readiness and psychological wellbeing of 15 male primary school students prior to transitioning to a secondary boarding school (S1) located away from home and family. A mixed-methods approach was used (i.e., online questionnaire and focus group), and findings indicate that while participants were apprehensive about expectations, study and encountering new technology at boarding school, all viewed the impending transition to S1 as a positive opportunity in their educational journey. Participants reported academic motivation and self-regulation above the norm; however, both questionnaire and focus group data indicated their academic self-perception was low. Levels of reported psychological distress were low, with symptoms associated with emotional problems, conduct problems, hyperactivity, peer problems, prosocial behaviour and overall total difficulties all found to be within the normal range. Indicators of life satisfaction and protective factors associated with resilience were similarly found to be within the normal range. Four major themes and eight subthemes emerged from the qualitative data, including: (1) enthusiasm (i.e., confidence, sadness); (2) opportunity (i.e., new experiences and choices, friendships); (3) anchor points (i.e., older siblings, orientation); and (4) expectations (i.e., study, technology). The findings of this study add to the literature encouraging staff in boarding schools to view transition through the lens of the early to mid-adolescence developmental period and the emergence of co-occurring innate psychological needs-in particular, the desire for competence, autonomy and relatedness. Strengths and limitations of this study are presented.