While existing literature documents disparities in and implications of absenteeism and truant behavior, less is known about truancy as defined in state laws. Habitual truancy, which can trigger external punitive responses, is particularly underexplored. The current study utilizes administrative data from the universe of Pennsylvania schools to examine longitudinal trends and school-level characteristics associated with habitual truancy between the 2010-11 and 2017-18 school years. Our findings indicate an increasing pattern of overall habitual truancy rates between 2010-11 (9%) and 2017-18 (13%). Habitual truancy rates are highest among Black and Hispanic students and in middle and high school grades. OLS regressions show that habitual truancy is positively associated with the share of students in a school who are Black and who qualify for free or reduced-price lunch, and higher exclusionary discipline and school police presence; and negatively associated with magnet schools. Our findings have implications for understanding patterns and predictors of habitual truancy and provide some insight into who might be subjected to punitive responses to habitual truancy in accordance with state policies.