The purpose of this study was to investigate the perceptions of preservice candidates and middle school tutees about working in an applied tutoring field-based experience and to see if and in what ways candidate beliefs were influenced by learner perspectives and feedback. Participants were four triads of preservice candidates and adolescent diverse learners. The tutoring dynamics of four triads were examined to find out what aspects of their relationships helped the tutoring process. Tutee interview, tutor reflection journals, and triadic session observations were analyzed and reported. A conceptual framework was presented to examine the changes over time of tutors'' perceptions of tutoring diverse learners; changes were analyzed through tutor electronic journal entries. It was concluded that the tutoring relationship is important to subsequent learning for both tutor and tutee. Results indicated the majority of preservice candidates exited the tutoring program with a transformation in their beliefs on teaching diverse learners and a positive tutoring field-based experience.