We assessed how high school dropouts in Croatia interpret their school experiences and life circumstances, using semi-structured interviews of 20 young people, M (SD) = 18.4 (1.23) years, 63.6% male, based on questions following a chronological life course from elementary to high school. Using qualitative content analysis and cluster analysis, we yielded a typology of high school dropouts. Four high school dropout types were identified based on the factors leading to dropout: (a) the poor academic achievers, (b) the quiet dropouts, (c) the maladjusted dropouts, and (d) the stressed dropouts. Our findings confirm the previously reported role of poor academic achievement and externalizing problems in high school dropout and additionally highlight the importance of internalizing problems and highly stressful life events for dropout risk.