Teacher retention continued to pose significant challenges to educational quality and institutional stability in Luweero District secondary schools. While transactional leadership remained the predominant management approach in many educational institutions, its specific effects on teacher retention remained insufficiently documented in the Ugandan context.This study employed a descriptive cross-sectional survey design involving 138 respondents from four selected secondary schools in Luweero District. The sample comprised 4 school principals, 4 deputy principals/supervisors, 70 senior teachers, and 60 junior teachers, selected through purposive and random sampling techniques. Data were collected using structured questionnaires and analyzed using SPSS version 25, employing descriptive statistics, correlation, and regression analyses. The findings revealed a moderate positive relationship between transactional leadership and teacher retention (r = 0.542, p < 0.001). Contingent reward demonstrated a significant positive effect (r = 0.598, p < 0.001), while management-by-exception (active) showed a weaker positive relationship (r = 0.387, p < 0.001). Management-by-exception (passive) exhibited a negative correlation with retention (r = -0.312, p < 0.001). Regression analysis indicated that transactional leadership explained 29.4% of variance in teacher retention. Transactional leadership significantly influenced teacher retention, though less strongly than transformational approaches. Contingent reward practices positively affected retention, while passive management styles undermined teacher commitment. The moderate explanatory power suggested that transactional leadership alone proved insufficient for optimal retention outcomes. School administrators should integrate contingent reward systems with broader leadership approaches, minimize passive management practices, and consider complementing transactional strategies with transformational leadership behaviors to maximize teacher retention.