To examine whether learning difficulties play a role in depressive symptoms, 658 Finnish adolescents were asked to complete scales for depression three times during the transition to post-comprehensive education. They also reported on their learning difficulties and feelings of inadequacy as a student. The results showed that learning difficulties prospectively predicted depressive symptoms. Moreover, the impact of learning difficulties was mediated via inadequacy as a student: learning difficulties predicted feelings of inadequacy as a student which, in turn, contributed to greater increases in depressive symptoms. Finally, gender moderated the association between learning difficulties and depressive symptoms: both being a girl and having a high level of learning difficulties predicted a higher initial level of depressive symptoms. (Contains 2 tables and 2 figures.)