Taking the UK and Japan as contrasting national case studies, this article supplements existing research into student migration by consolidating a regulatory perspective with individual narrative accounts. Reported here are the results of a mixed-methods two-phase study. Phase 1 is a concerted trajectory analysis of student migration policy in the UK and Japan from 2004 to 2018, while phase 2 draws on biographical-narrative interviews with 26 student-migrants. The paper reveals tangible effects of the receptivity, stability, and transparency of regulatory frameworks in student-migrants' trajectories, while also demonstrating that seemingly receptive regulatory environments do not necessarily equate to smooth and risk-free post-study transitions.