Using a nationally representative sample of Head Start recipients, this study compared Head Start classroom contexts and English language and literacy skill trajectories for Spanish-speaking dual-language learners (DLLs) and English speakers from preschool through kindergarten. It also examined whether Head Start classroom characteristics were differentially associated with skill development across groups, both concurrently in Head Start and longitudinally in kindergarten. Results indicated that classroom characteristics tended to be similarly associated with skills across language subgroups. Regardless of language status, children whose classrooms were instructionally supportive and not overly managed tended to have higher language and/or literacy skills in Head Start. Children whose Head Start classrooms had higher Emotional Support and were not overly managed had higher kindergarten language skills. Child-initiated activities were associated with higher language skills, whereas teacher-directed activities were related to higher literacy skills. DLLs benefited more from Emotional Support and child-initiated activities in some skills. Practice or Policy: If replicated, findings have practical implications for Head Start professional development and classroom practices. Specifically, teacher professional development might focus more intensively on improving Emotional and Instructional Support, and teachers and program administrators might consider allocating more time to child-initiated and teacher-directed activities to build specific skills. (author abstract)