Background: The mental health of students in UK higher education (HE) is receiving increased attention, and support services for students are under increased pressure. Aims: Drawing on ecological systems theory (EST), this study sought to explore possible contextual influences, over time, on student distress within HE. Method and Samples: We conducted a two-stage Delphi study, first asking UK professionals (n = 236) from primary, secondary, further education, and HE to provide possible reasons for increases in student distress. The material was reduced to 58 representative statements across all sectors with a further 10 specific to HE. In stage 2, 89 participants rated each statement in terms of whether it: (1) takes place and (2) contributes to distress. Results: The results suggest multiple contextual influences potentially contributing to student distress. They can be summarized using the words: cuts, competition, and comparison. Education professionals in our sample reported that, upstream from HE, pressures on schools and colleges have led to a narrowing of curricula, with a more singular focus on assessment. Reduced teaching teams and pressurized staff unintentionally embed an assessment focus within students who unhelpfully compare themselves with peers while also struggling with wider societal cuts, austerity, and political uncertainty. Conclusions: The discussion draws on the peer-reviewed literature and relevant reports, discussing them in the context of EST, finding considerable support for these influences. The potential importance of adopting a contextual approach and incorporating this knowledge into the way we understand and tackle students' distress and their preparedness for HE is discussed.