Kindergarten teachers are confronted with an evolving context for teaching and assessment. Recent reforms throughout the world have resulted in two fundamental shifts: (a) a growing emphasis on academic learning and increased use of assessment to support and monitor students' academic and developmental progress and (b) the use of play as a dominant pedagogical approach. Across these shifts, little research has been conducted on the integration of assessment with play-based learning to support teachers' practices. The present study addresses this gap by presenting empirical data from 20 purposefully selected kindergarten classrooms on how teachers (a) conceptualize the relationship and challenges between assessment and play, (b) enact assessment practices, and (c) address challenges implementing assessment during play. Results of this study demonstrate the various ways assessment and play can operate within kindergarten education to support student learning while providing an empirical foundation for future research into early primary assessment theory and practice.