Since the collapse of the economic bubble, Japanese schools have been challenged to respond to extensive changes in the students and communities they serve. As a result, research on the education system published only a few years ago may not accurately capture current conditions in the schools. This is especially true in the area of student guidance, which has undergone significant modification in recent years. This article documents those changes. Drawing from an ethnographic study conducted over a six-year period, it examines guidance practices in contemporary Japanese middle schools. The objective of the study was to document shifts in student attitudes toward school and to analyze the effects of the revised mentoring practices. Recently, ministries of education throughout Asia have been promulgating reform policies that aim to alleviate academic pressure in the schools. Research that examines the effects of those policies, however, has largely ignored the role that student guidance plays in the education process. The findings presented in this article can therefore inform decision-making related to guidance practices in contemporary Japanese schools, and in other settings that are attempting to concomitantly reduce the academic stress experienced by adolescents and maintain a sense of order in schools.