This study explored the extent to which parents were able to scaffold their children's Self-Regulated Learning (SRL) in the context of authentic academic tasks and attempted to identify specific dimensions within the parent–child interaction (socioemotional and instructional) that were related to children's SRL. Fifteen Chilean parents and their underachieving primary-aged children participated in set of six SRL-enhancing activities in the areas of reading comprehension and mathematical problem solving. Individual assessments of children's SRL in the same curriculum areas were carried out before and after these activities. The assessment outcomes revealed that, although at the group level children showed positive changes in some aspects of SRL (metacognitive knowledge and regulation of cognition), individual variation was also noticeable within the group. Children's evidence of SRL during the parent–child activities was related to both social and instructional dimensions of the interaction. SRL posttest outcomes, however, showed stronger associations with instructional behaviors.