The transition from primary to intermediate school represents a significant period of change and opportunity for early adolescents, who must adjust to an unfamiliar environment while also navigating a critical developmental milestone: the onset of puberty. Many students face social, academic, and emotional challenges that can impact their overall wellbeing. Despite its significance, research has predominantly focused on other school transitions, leaving a gap in understanding students’ lived experiences. Informed by the Transactional Model of Stress and Coping and Resilience Theory, this qualitative research explored students’ reflections on their transition, focusing on their expectations, adjustment, and coping. It also examined students' perspectives on the Graeme Dingle Foundation’s Kiwi Can program and its application to their primary-intermediate school transition. Ten year-seven students participated in semi-structured interviews, and students’ primary caregivers completed a questionnaire with similar open-response questions as the student interviews for a supplementary data source. The findings revealed that students primarily held negative expectations about intermediate school, often shaped by external sources. Social concerns were particularly salient; however, the extent of peer conflict and complex social dynamics was unexpected. Although academic difficulty increased, the changes were often overestimated. A positive aspect of the transition to intermediate school was the opportunity to participate in extracurricular activities and novel subjects, fostering self-expression. Students were proficient at identifying their coping strategies, particularly relying on peer support and self-directed emotional regulation. Some students attributed their application of resilience and social-emotional skills to Kiwi Can, while others did not consciously make direct links. Findings on expectations, lived experience, and coping aligned with literature on intermediate transitions, offering rich qualitative insights to inform practices and policies that promote a smooth transition.