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Previous research has identified students' personality traits, especially conscientiousness, as highly relevant predictors of academic success. Less is known about the role of Big Five personality traits in students when it comes to teachers' decisions about students' educational trajectories and whether personality traits differentially affect these decisions by teachers in different grade levels. This study examines to what extent students' Big Five personality traits affect teacher decisions on grade retention, looking at two cohorts of 12,146 ninth-grade and 6002 seventh-grade students from the German National Educational Panel Study. In both grade levels, multilevel logistic mediation models show that students' conscientiousness indirectly predicts grade retention through the assignment of grades by teachers. In the ninth-grade sample, students' conscientiousness was additionally a direct predictor of retention, distinct from teacher-assigned grades. We discuss potential underlying mechanisms and explore whether teachers base their decisions on different indicators when retaining seventh-grade students or ninth-grade students.