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Prior research has shown that preschoolers’ absenteeism is negatively associated with their development. Using Head Start FACES data, this study examines the conditions under which preschool absenteeism matters more by incorporating the role of classroom quality (CQ) and household stimulation (HS). Results showed that associations with language, literacy, and approaches to learning skills varied by levels of CQ experienced. Moreover, high HS buffered the negative associations between absenteeism and only children’s literacy skills. Finally, no meaningful differences emerged when considering children’s absenteeism, CQ, and HS jointly in relation to children’s developmental outcomes. Findings highlight the importance of considering how the classroom environments they are missing and the home environments they are experiencing when absent from school matter for preschoolers’ development.