Kindergarten education is changing. Current reforms have increased accountability structures requiring teachers to integrate assessments throughout their instruction to support academic learning while retaining developmentally appropriate pedagogies such as play-based learning. Despite these reforms, comparatively little research has been conducted on teachers' assessment practices within play-based instructional contexts. The purpose of this study was to explore teachers' approaches to assessment in play-based kindergarten education and specifically to examine how assessment practices differed based on teachers' conceptions of the purpose of play in student learning. Data were obtained from 77 Ontario kindergarten teachers via (a) an electronic survey, (b) in-depth interviews, and (c) classroom observations. Overall, data from this study suggest a misalignment in teachers' perspectives of the purpose of play and what teachers assess during periods of play.