This project examines the supervisory roles and clinical experiences in a School of Education program that offers multiple pathways to licensure, including the Transition to Teaching (T2T) alternative route to certification program. Through our reflective supervisory and instructional experiences within this program, we explore the unique challenges in supervising non-traditional adult learners entering into teaching after experience in various professional disciplines. We use a Critical Whiteness Studies lens to create a composite narrative of these experiences as an approach to 1) better understand adult learner dispositions; 2) contribute to research pertaining to the field of educational supervision and clinical experiences in an the under-researched area of alternative certification programs; and 3) provide field-based social justice-oriented practices grounded in critical reflection, discussion, and praxis for supervisors who work with adult learners in urban elementary contexts.