Based upon a series of interactions between the researcher and students, this study examines the educational issues of remote areas in Taiwan. In the spirit of case study method, we compile data from direct listening, observations, and interviews of students, teachers, and parents. These narrative data are then analyzed through the lens of cultural and social capital as well as the educational problems of disadvantaged students in remote areas. Our approach of using first-hand descriptions from different parties is expected to break through teachers' middle-class mindset and decompose the educational problems of remote areas. We find that students' problems are rooted in their specific background, environment, and experiences; and hence, strategies for positive discipline should be developed and revised accordingly. Finally, we propose effective instructional strategies for positive discipline and counseling and offer several suggestions for educators' and policymakers' references. Hopefully, the subsequent implementation and feedback of these testable strategies can enhance our understanding of educational issues in remote areas and eventually benefit the disadvantaged students there.