Teacher-facilitation of play is proposed as an effective method for supporting early literacy learning, however, educators remain uncertain how to balance child-autonomy in play while also directing play toward explicit academic objectives. In response, this study sought to understand how kindergarten teachers can successfully facilitate play to support early literacy development. Classroom observations and semistructured interviews were gathered and qualitatively analyzed to identify key perspectives and classroom practices that lead to the educators' successful facilitation of play to support literacy. Results of this study showed how different core literacy skills can be supported through different types of play, with each offering unique and critical opportunities for learning. Results also demonstrated how a multitude of core literacy skills can be supported through guided approaches to play, and begin to illustrate how teachers are facilitating a continuum of guided play to support literacy learning.