The study examines school and parental influences on adolescents' occupational exploration. Analyses of data from 859 6th, 8th, and 10th graders attending high- and lower-track high schools in the German federal state of Thuringia suggested more extensive exploration among students closer to the school-to-work transition. Besides cross-sectional effects of parenting and achievement orientation at school, acceptance and openness students experienced in class predicted increases of their exploratory behaviors. Multilevel analyses showed, however, that school effects operated on the level of subjective perceptions (individual level), but not on the level of intersubjective reality (classroom level). Implications for attempts to foster and facilitate exploration are discussed. (Contains 3 tables.)