The present study was designed to investigate the relationships between role strains following the transition to secondary school and academic achievement. Academic engagement was hypothesized to mediate between role strain and achievement. The sample consisted of 749 students in their first year of secondary school. Four types of role strain were investigated: parent, teacher, school and peer. Parent and teacher role strains appeared to be negatively associated with academic achievement, as mediated through academic engagement. Parent and school role strain were directly and negatively associated with achievement. Results are discussed in the light of parenting practices and the developmental mismatch hypothesis.