Research Findings: We examined whether Head Start teachers’ depressive symptoms are associated with their engagement in high-quality conversations with children, and we considered the extent to which this association is consistent across classroom contexts and activities. Observations of Head Start teachers’ conversations with children were conducted using a teacher-focal coding system and teachers reported on depressive symptoms. Generalized estimating equations were used to test study hypotheses. Teachers’ depressive symptoms were negatively associated with the likelihood that a high-quality conversation would occur during an observation interval. The relation between teacher depressive symptoms and high-quality conversations was negative during both structured settings and free choice settings. This relation also remained negative during play (e.g. art, music) and routine (e.g. personal care, clean up) activities. However, the relation between teacher depressive symptoms and high-quality conversations was not significant during academic activities (e.g. math, books, language). Practice or Policy: Potential explanations, strengths and limitations, and implications for study results are discussed. (author abstract)