Purpose: The rationale for teacher-focused graduate education encompasses diverse motivation, including: enhance salaries, elevate professional status, meet licensure requirements, and improvement of teacher effectiveness (professional development). Despite the proliferation of graduate programs for in-service educators, their impact on teachers, their contexts (schools), and their students remains unclear. This study explored graduate student experiences within a Health and Physical Education Masters of Education cohort. Method: Employing Dewey’s theory of experience and interpretive inquiry, interviews were conducted with students after the first year (n = 11) and upon program completion (n = 10). Interviews were transcribed, coded, and themed. Results: Students expressed deep experiences of growth, reflection, and challenges, which were organized into four themes: (a) theory to practice and back again, (b) multiple perspectives, (c) becoming a community, and (d) transforming purpose. Discussion/Conclusion: The findings inform new cohorts, graduate programs, and future work on a Deweyan framework for graduate studies in Health and Physical Education as transformative professional learning.