School orientation constitutes a decisive stage in students’ educational trajectories, influencing their motivation, academic achievement, and future professional prospects. Although this choice should ideally be guided by each student’s personal aspirations, abilities, and interests, it is often shaped by a range of external factors, notably familial, economic, cultural, and geographical influences. In many contexts, orientation decisions do not result from a free and informed process but rather from sometimes constraining influences exerted by parents, teachers, or the social environment. This study examines the dynamics of school orientation in two contrasting contexts: urban and rural settings. It aims to highlight the impact of variables such as family income, parents’ level of education, their educational attitudes and expectations, as well as students’ perceptions of their own abilities and career prospects. Through a comparative analysis, the study seeks to understand how these factors, depending on the context, contribute to either enhancing or constraining students’ freedom of choice in their educational pathways.