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The purpose of this qualitative study was to explore perceptions of and experiences with truancy for teachers and students in one urban Midwest high school with a focus on the Career Pathways program as a potential way to reduce truancy. The three research questions guiding the research were as follows. First, what are the perceptions of a small sample of truant students aged 18 years and older about school and other factors related to their own truancy? Second, to what extent do truant students perceive that elements of the Pathways program would be a solution to truancy? And third, what are the perceptions of a small sample of teachers about the factors related to truancy and solutions to truancy? Student participants in the study believed the top three reasons they felt their classmates did not attend school were because of student employment, mental health, and a lack of motivation. Students missed school not because they did not like being there but because there were certain antecedents that led to their absences, such as in-school and out-of-school suspension, anxiety, and bullying. Teacher participants felt overwhelmed and even exhausted from dealing with multiple students who were chronically truant. Some teachers felt their mental and physical health were compromised, so they began to set boundaries to preserve their health. One recommendation based on the study is the implementation of an onsite comprehensive school-based mental health program for teachers and students. Another recommendation is to implement career pathways with work-based learning and the implementation of mentorship for incoming ninth graders.