In this paper, early childhood teacher educators describe their work to provide opportunities for pre-service teacher candidates to engage in specific practices that facilitate reflection and planning related to enhancing toddlers' engagement during free play. The practices targeted were structured by the instructor and supported by the mentor teacher and included observation; guided written reflection; collective discussion and reflection; and intentional planning. Each practice and how it was implemented and completed by the instructor and students are discussed. As a result of participating in the practices, teacher candidates identified several factors they believed impacted toddlers' engagement during free play. They included location of centers, materials, and other people, variety of materials, adult interaction, and children's interests, all of which aligned with prior research. Implications for practice for pre-service teacher preparation programs and practicing teachers are provided.