Background: The recent influx of Newly Arrived Migrant Students (NAMS) in Western-European societies poses important educational questions about how best to support migrant students within the education system. Purpose: We sought to study how elements that are associated with cultural capital–namely a sense of entitlement and strategic knowledge–have relevance to NAMS’ educational trajectories. In studying the process of how cultural capital relates to educational careers, this study argues for a general shift from a resource-focused approach towards a strategy-focused approach to cultural capital. Sample: We collected data from 33 NAMS from six secondary schools in a city in Flanders (the Dutch-speaking part of Belgium). A maximum difference approach was used: this allowed comparison of NAMS who followed the most academic track (general track) and the least academic track (vocational track) in secondary education in Flanders. Design and methods: We undertook 33 in-depth biographical interviews during which the NAMS reconstructed their educational trajectories. Data were analysed qualitatively. We used structural approach analysis to identify each narrative’s core structure. These structured fragments were then thematically coded. Results: Within the categories ‘a sense of entitlement’ and ‘strategic knowledge of the education system’, the analysis detected differences in strategies of action between pupils in the general track and in the vocational track. Conclusion: The findings offer insights that could support the development of better strategies to guide and support NAMS in education. As NAMS’ integration in the educational system appears to be a stretched and slow process of orientation, studying their trajectory has the potential to deepen our understanding of known mechanisms of the reproduction of inequalities in education.