Background <p>National attention on teacher stress has exploded amidst record teacher shortages after COVID-19. Teacher stress has ramifications not only for teachers’ own wellbeing, but also for their students’ classroom experiences. More research is needed on a wider set of teacher stressors and their links to classroom quality, assessed before and after COVID-19.</p> Objectives <p>The current study addresses this gap by exploring associations between teacher stressors and classroom quality before and after COVID-19.</p> Methods <p>We leveraged rich data from a study following a cohort of children in public elementary schools in Tulsa, Oklahoma. Children’s first-grade teachers (<i>n</i> = 114) were surveyed in early 2020, before COVID-19 onset, and their third-grade teachers (<i>n</i> = 87) were surveyed in 2022, after COVID-19 onset. We examined the prevalence of stressors and links between these stressors and multiple facets of classroom quality in each group.</p> Results <p>Teachers reported a high prevalence of emotional, health, and economic stressors both before and after COVID-19. Multivariate regression analyses yielded no significant associations with quality before COVID-19; associations between stressors and quality after COVID-19 were weak and inconsistent.</p> Conclusions <p>Further work is needed to understand the range of teachers’ stressors and how they might relate to classroom learning conditions. Even absent associations, documenting teachers’ experiences informs current debates about teacher retention, wellbeing, and learning recovery.</p>