There is a considerable amount of research investigating students’ transition from college to university but it is important this focus is directed specifically towards the transition of international students, as the difficulties they face are profound. The literature surrounding international students seems to lack an in-depth understanding of how multiple contextual factors influence how students adjust to Higher Education. Therefore, the present study utilizes Bronfenbrenner’s (2009) ecological theory of human development in order to understand both immediate and distal environmental influences and how they interact to impact on the individual’s development from a holistic perspective. Five international students participated in a time line interview. Findings suggest that international students face a number of challenges when transitioning from their home country to study in higher education in the UK, particularly in the areas of language competence; cultural assimilation and social relationships. This in turn prevented meaningful learning occurring. Applying Bronfenbrenner’s theory, the participants’ broader environment was analysed, which encouraged an examination of the challenges they faced which regards to cultural influences, government influences and university policies, as well as influences from within their immediate environment.