Characteristics of cooperating teachers that lead to successful student teaching experiences and the benefits accruing to cooperating teachers were investigated in a case study. A unique aspect of this study was the focus on the use of cooperating teachers who are alumni of the teacher education program investigated. Cooperating teachers were surveyed and interviewed concerning what had best prepared them for being cooperating teachers, what benefits they gained from the experience, and what differences were found in working with student teachers from their own pre-service preparation program compared to other programs. Evidence-based conclusions indicated: (1) the most important factor in making an effective cooperating teacher is being prepared as a reflective practitioner; (2) the strongest benefit of being a cooperating teacher is having the chance to become more reflective about one's own practice; and (3) the most successful experiences for the cooperating teacher result when there is a strong alignment of theory and practice between the cooperating teacher and student teacher. Recommendations for using alumni cooperating teachers where possible, providing thorough preparation in the expectations of the program for non-alumni teachers, and encouraging means to develop close relationships between cooperating and student teachers are discussed.