Understanding the reasons that individuals drop out of high school is fundamental to improving intervention efforts to promote graduation. The authors present a mixed methods analysis of the reasons individuals drop out of high school before graduating. Using a survey methodology with young adults who left school before graduating (N = 1,047, M age = 21.5 years, SD = 2.2 years, age range =18-25 years), the authors assessed ongoing life stressors, as well as the turning points individuals identified as the top reason for why they left school. Qualitative analysis provided seven categories of turning points: mobility, family, peers, school engagement and environment, health, crime, and multiple categories. More than half of respondents indicated that the reason they dropped out was related to school engagement and environment. Results showed differences across profiles of lived experiences, reported turning points, and sex.