International students often require extracurricular assistance upon arrival in the host country. Many universities operate programs pairing international and domestic students for academic and adjustment assistance. The tutor system operating at Japanese national universities has similar objectives. Although the literature has highlighted several problems with the system, it is viewed as a viable form of educational assistance. This study examined the data from 38 interviews with tutors, international student tutees, and administrators, qualitatively analysing the perspectives of these stakeholders to uncover the main factors determining program effectiveness. Data analysis revealed several main themes relating to tutoring effectiveness, and differences were found in how tutors and tutees perceived their participation in the system. Although tutees tended to focus on the interpersonal relationship, tutors were more concerned about their tutoring ability. Implications of the findings are discussed for enhancing peer-pairing programs to better accommodate the needs of students.