Research Findings: This observational study of preschoolers (N¬ =¬ 140) in their classrooms (N¬ =¬ 41) examined variation in teacher orienting (defined as explanations and demonstrations about the procedures and rationale behind activities, including center projects, to the whole group or to individual children) and associations between orienting and children's academic and self-regulation skills. Orienting to individual children rarely occurred, but significant variation between classrooms in whole-group orienting was present. Children who experienced higher amounts of whole-group orienting had higher scores on general knowledge, mathematics, emergent literacy, and self-regulation in the spring when we controlled for child- and classroom-level background variables, including children's fall pretest scores, teacher education, and experience. For expressive vocabulary, greater exposure to orienting predicted higher spring vocabulary for younger but not older preschoolers. Practice or Policy: The results indicate the importance of reducing classroom disparities in children's preschool experience and suggest that more attention should be paid to teachers' efforts to explain upcoming activities in whole-group settings. Finally, the interaction between orienting and child age for vocabulary suggests the need to consider both child characteristics and aspects of the context to identify the optimal preschool experiences for individual children.