This study explored the influence of organizational support and teachers workload on school heads caring leadership and teachers well-being. It aimed to determine whether there is a significant relationship between caring leadership in schools and teachers well-being. Additionally, the study examined the mediating effect of organizational support on the relationship between school heads caring leadership and teachers well-being. It also investigated whether teachers workload significantly moderates this relationship. A descriptive correlational design was employed, involving 230 teachers from two districts in Candelaria, Quezon. Data were collected using a validated survey questionnaire. Statistical analyses included frequency, percentage, mean, standard deviation, Pearson r, and multiple regression analysis. Results indicated that school heads caring leadership, teachers well-being, and organizational support were all at high levels, while teachers workload was at a normal level. Furthermore, a positive association was found between school heads caring leadership and teachers well-being. A significant correlation was also found between school heads caring leadership and organizational support. Organizational support showed a significant positive relationship with teachers well-being and fully mediated the relationship between school heads caring leadership and teachers well-being. However, teachers workload did not significantly moderate this relationship. The study recommends enhancing caring leadership training for school heads, strengthening organizational support structures, fostering collaboration and peer support, and monitoring and balancing teachers workload.