Newcomer adolescents make up a large minority of Canada's population and their positive integration experiences with education systems across the country are critical for both their development and the country's long-term success. The current study examined newcomer adolescents' (n = 4, between 16 and 18 years old) integration experiences using an arts-based engagement ethnography to understand what influences their positive integration into the school system. Artifacts, interview, and focus group data were analyzed systematically using ethnographic research guidelines. Five structures were identified: (1) barriers to advancement at individual, school, and macro levels, (2) fluctuating relationship with cultural identity, (3) limited trust in systems, (4) resilience through independent learning, and (5) facilitating factors to positive integration experiences at the family and school level. In keeping with a relational developmental systems theory framework, each structure accounts for multiple inter- and intra-individual factors at multiple environmental levels. These findings outline considerations for systemic issues in academic institutions and offer suggestions for how institutions can better support newcomer adolescents.