School attendance problems, including school absenteeism, are common to many students worldwide, and frameworks to better understand these heterogeneous students include multiple classes or tiers of intertwined risk factors as well as interventions. Recent studies have thus examined risk factors at varying levels of absenteeism severity to demarcate distinctions among these tiers. Prior studies in this regard have focused more on demographic and academic variables and less on family environment risk factors that are endemic to this population. The present study utilized ensemble and classification and regression tree analysis to identify potential family environment risk factors among youth (i.e., children and adolescents) at different levels of school absenteeism severity (i.e., 1 + %, 3 + %, 5 + %, 10 + %). Higher levels of absenteeism were also examined on an exploratory basis. Participants included 341 youth aged 5–17 years (M = 12.2; SD = 3.3) and their families from an outpatient therapy clinic (68.3%) and community (31.7%) setting, the latter from a family court and truancy diversion program cohort. Family environment risk factors tended to be more circumscribed and informative at higher levels of absenteeism, with greater diversity at lower levels. Higher levels of absenteeism appear more closely related to lower achievement orientation, active-recreational orientation, cohesion, and expressiveness, though several nuanced results were found as well. Absenteeism severity levels of 10–15% may be associated more with qualitative changes in family functioning. These data may support a Tier 2-Tier 3 distinction in this regard and may indicate the need for specific family-based intervention goals at higher levels of absenteeism severity.