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Preschool absenteeism rates are high. Children with higher absenteeism rates perform worse on assessments of literacy, math, and social-emotional skills by the end of a school year and are more likely to be absent in subsequent years than their peers with lower absenteeism rates. Nevertheless, little is known about the predictors or longitudinal consequences of preschool absenteeism, or about approaches for prevention. In this dissertation, I use Bronfenbrenner’s ecological systems model to inform a more holistic understanding of children’s absenteeism during preschool and through early elementary school. In Paper 1, I use statewide administrative data from the Massachusetts Department of Elementary and Secondary Education to examine patterns of absenteeism from preschool through the early elementary years and whether these absenteeism patterns are associated with children’s academic outcomes in Grade 3. Given prior evidence showing particularly high absenteeism among low-income children, in Papers 2 and 3, I home in on preschool absenteeism among a sample of low-income children enrolled in Head Start programs—using the Head Start Family and Child Experiences Survey, 2009 cohort. In Paper 2, I focus on understanding who is most likely to be absent by using latent profile analysis to identify profiles of household risk factors and their associations with absenteeism. I then examine which family engagement factors (e.g., parents’ satisfaction with Head Start, Head Start programs’ provision of family support services) can be used to reduce absenteeism and for whom these factors are most effective. Finally, In Paper 3, I address the conditions under which preschool absenteeism may matter more for children’s learning and development. Specifically, I move beyond estimating average associations between absenteeism and children’s developmental outcomes by examining these associations in the presence of varying levels of classroom quality and household stimulation. Together, the findings of these papers not only address basic questions such as “Does absenteeism matter” but also push the literature on preschool absenteeism forward by examining questions like “How does absenteeism change over time and how do these changes matter for children’s outcomes?”; “Who is absent?”; and “For whom and under what conditions does absenteeism matter for children’s learning and development?”. Findings can support the development of more targeted and timely interventions for reducing absenteeism beginning as early as the preschool years.