Drawing on our projects of transition to mathematically demanding subjects in UK Higher Education and an extension of this work in Norway, we explore the measurement of various pedagogical and learning aspects of students’ transition into Higher Education. We focus on experiences of engagement, and alienation, which we claim can offer an enhanced view on student learning experiences. Our analysis is based on longitudinal surveys of students entering different programmes in UK (N = 1778), and Norwegian (N = 721) universities. Validation is performed within the Rasch measurement framework, which indicated problems in establishing measurement invariance. Cross-sectional analysis of the two datasets, then, revealed consistent patterns in the process of alienation from mathematics as well as some systemic mechanisms that can help alleviate that.