This open-access article from the Journal of Research on Educational Effectiveness shares findings from a longitudinal study about changes to teacher working conditions from the 2016–17 to 2022–23 school years. Previous research shows that teacher working conditions are a top priority among other job-related factors and are related to teacher retention and turnover rates. The article analyzes data from about 127,000 Illinois teachers’ 5Essentials surveys to identify trends in teachers’ self-reported working conditions before, during, and after the COVID-19 pandemic. Overall, the findings present slight improvement before the pandemic, then declining teacher working conditions over the years, with the largest declines occurring after the pandemic. More specifically, teachers report worse working conditions related to perceived safety, interactions with students and families, and trust among teachers, principals, and parents. Researchers, policymakers, and school leaders may find this study helpful in examining job-related factors that contribute to teacher turnover in order to move toward sustainable solutions for retention.