This study examined how children's insecure internal representations of interparental and parent-child relationships served as explanatory mechanisms in multiple pathways linking interparental conflict and parent emotional unavailability with the emotional and classroom engagement difficulties the children had in their adjustment to school. With their parents, 229 kindergarten children (127 girls and 102 boys, mean age = 6.0 years, SD = 0.50, at Wave 1) participated in this multimethod, 3-year longitudinal investigation. Findings revealed that children's insecure representations of the interparental relationship were a significant intervening mechanism in associations between observational ratings of interparental conflict and child and teacher reports on children's emotional and classroom difficulties in school over a 2-year period. Moreover, increased parental emotional unavailability accompanying high levels of interparental conflict was associated with children's insecure representations of the parent-child relationship and children's difficulties in classroom engagement at school entry. The findings highlight the importance of understanding the intrinsic processes that contribute to difficulties with stage-salient tasks for children who are experiencing interparental discord.