The present study examined the relationship between school absenteeism severity and specific clinical and family variables in middle and high school youth aged 11-19 years recruited from two truancy settings. School absenteeism severity was defined as a percentage of full school days missed from the current academic year at the time of assessment and was examined both dimensionally and categorically at various levels. Greater absenteeism severity, measured dimensionally (0-100%) as well as across various categories, was expected to be associated with (1) greater internalizing symptoms (general anxiety, separation anxiety, social phobia, panic, obsessions and compulsions, and depression), (2) greater externalizing symptoms (inattention/ hyperactivity, rule-breaking behavior, and aggressive behavior), and (3) greater family conflict and lower active-recreational orientation. Categorical analyses revealed more nuanced findings, specifically that students with 15-60% absenteeism displayed more internalizing symptoms than those with less or greater absenteeism. The findings are discussed with respect to possible demarcation of Tier 2 and Tier 3 points for students with problematic absenteeism as well as interventions that may apply to each.