Using latent variable path analysis with partial least squares (LVPLS), the study examines the pathways between parenting practices and children's motivational orientation toward school work over the transition to middle school. Greater external control and lack of guidance by parents in the 5th-grade year were related to children's poorer academic achievement that year, which in turn predicted a more extrinsic motivational orientation in 7th grade. In contrast, greater parental autonomy-supporting behavior in the 5th-grade year was related to children's higher academic achievement that year, which in turn predicted a more intrinsic motivational orientation in 7th grade. In all instances, children's perceptions of their academic competence mediated the relation between 5th-grade academic performance and 7th-grade motivational orientation.