Students' different educational pathways were examined in relation to their disengagement during adolescence. The participants were Icelandic youth (N = 832) who were followed from age 14 to 22. Based on their academic achievement at age 15 and educational attainment at age 22 they were classified into groups that took expected versus unexpected paths. The findings indicate that adolescents' behavioral disengagement (negative school behaviors) and emotional disengagement (academic disinterest, disidentification with school) differentiated according to their pathways. At age 14, those "at risk" academically who graduated unexpectedly showed fewer negative behaviors than the expected dropouts. Moreover, high achievers who dropped out unexpectedly showed more behavioral (negative behaviors) as well as emotional (academic disinterest, disidentification with school) disengagement compared to expected graduates. The following year (age 15), in general, disengagement increased among unexpected dropouts but decreased among expected graduates. Males and students from lower-SES backgrounds were generally more disengaged, and males from those backgrounds became more emotionally disengaged during their last year in compulsory school. (Contains 5 tables.)