Student absenteeism and disengagement from school have for more than a decade reflected entrenched problems within the Ontario school system, resulting in diminished capacity for student academic achievement. Marginalized, African Canadian, and lower socioeconomic students are the most affected. Through a mixed-methods approach utilizing both qualitative and quantitative research involving 313 students in a survey component and 40 students in 6 focus groups, the researcher explores the antecedents behind student absenteeism and disengagement from the learning process. Specific questions relating to student in-school experiences, thoughts and feelings, the impact of teacher attitudes, expectations and biases, and peer influence during critical educational stages in students' lives, produced contextually relevant opinions and observations from the students themselves. This is important as most research on school "drop outs" has omitted the salience of students' voices. Resultant themes derived from this study indicate the following implicating factors: (a) school leadership, (b) school culture and environment, (c) curriculum, (d) teacher attitude and expectations, and (e) peer pressure. The interplay of these influences causes either student engagement or disengagement which in turn affects student attendance. It is apparent from the research that the school in general and teachers specifically, either negatively or positively influence students, which suggests that both teachers and school administrators can help students improve their attendance, and thus their academic performance by establishing positive and influential relationships with them. This would have a profound effect on whether students succeed or fail. Study findings indicate that teaching pedagogy, a curriculum relevant to student life experiences, and a more hospitable and equitable school environment are crucial to whether a student becomes bored or passionate about learning. Changes to all three are essential, and recommendations are given in this regard.