Kindergarten teachers face the challenge of balancing traditional developmental programming and contemporary academic standards. In classrooms following a play-based learning framework, academic content such as literacy is to be taught within children's play. However, educators have reported conceptual and practical challenges with integrating play and literacy. Although the educative contexts of direct instruction, teacher-guided play, and child-directed free play have been individually examined and endorsed for promoting early literacy, the enactment of literacy behaviors across these contexts in kindergarten has not been widely examined. The current study investigated teacher perspectives on play and literacy development and the resulting integration of literacy behaviors across educative contexts. Semistructured teacher interviews and video data were collected in 12 participating classrooms. Results revealed three common challenges with integrating play and literacy learning: direct instruction plays a key instructional role, play is less structured and difficult to plan, and feeling uncertain how to implement guided play. These challenges were reflected in the differing frequencies of literacy behaviors observed across contexts. These results point to the need for additional research and teacher training with respect to implementing guided play for literacy learning, as well as strategies for balancing direct instruction with play-based approaches.