Research Findings: This study investigated the complexity of teacher questions in 14 preschool classrooms serving economically disadvantaged 4-year-olds. The purposes were to explore the frequency and complexity of teacher questions and to determine the extent to which question types varied for different classroom contexts. Using teacher utterances from 24-min transcripts of videotaped classroom observations, we used a logistic regression framework to determine the frequency of teacher questioning and the extent to which this related to classroom context. Results indicated that questions characterized 33.5% of all teacher utterances, with management questions occurring most frequently (44.8%), followed by more cognitively challenging questions (32.5%) and less cognitively challenging questions (22.7%). The frequency of use for the different question types varied by classroom context; specifically, management questioning occurred most frequently in teacher-directed and child-directed contexts, whereas more cognitively challenging questions occurred most frequently during shared storybook reading. Practice or Policy: This study has implications for the professional development of early childhood educators, particularly with respect to the use of questions as a language stimulation technique for preschoolers at risk for language- and literacy-related difficulties. (Contains 4 tables and 2 figures.)