Individuals with emotional and behavioral disturbances (EBD) and those attending special schools tend to have poorer adult outcomes than adolescents without EBD and peers from regular schools. Using a four-group comparison (students with or without EBD from special schools and students with or without EBD from regular schools), the present study examined whether German adolescents with EBD and adolescents attending special schools also have lower expectations regarding their transition to adulthood (moving out of parents' home, finishing postsecondary education, being full-time employed, getting married, and becoming parents) than adolescents without EBD and adolescents attending regular schools. Only small between-group differences were found regarding the expected timing of transitions and the anticipation to not attain transitions at all. Adolescents with EBD reported later expected ages of marrying and adolescents with EBD attending regular schools expressed later ages of being full-time employed. Students from special schools more often anticipated remaining unmarried. The results are discussed with concern to how adolescents' overoptimistic expectancies can be handled. Also, the instrumentality of confidence of success is considered. [An erratum to this article can be found at http://?dx.?doi.?org/?10.?1007/?s10212-016-0292-y.]