A person-centered approach was used to identify the profiles of symptoms of psychological ill-being among Finnish upper secondary education students (N = 2889); to examine whether gender and educational track (i.e., academic or vocational) are associated with these profiles; and to investigate the role of profiles in school dropout intentions. Using latent profile analysis, one asymptomatic profile (normative, 79.2%) and three symptomatic profiles (internalizing symptoms, 9.1%; externalizing symptoms, 9.1%; and comorbid symptoms, 2.6%) were identified. Boys in the vocational track were overrepresented in the externalizing-symptoms profile, whereas girls in both tracks were overrepresented in the internalizing-symptoms profile. Students in the three symptomatic profiles showed higher dropout intentions than those in the normative profile. Altogether, this study indicated that up to every fifth student experiences symptoms of psychological ill-being, and those exhibiting these symptoms might be at greater risk of dropping out of school than their peers.