The study focuses on the implementation of the "Catch-Up Fridays" program in the Davao del Norte Division, Philippines, aimed at addressing learning gaps among students exacerbated by the COVID-19 pandemic. Initiated by the Department of Education (DepEd), this program dedicates every Friday to reading and writing activities, values, peace, and health education to enhance students' academic and holistic development. Despite its noble intentions, the program faces challenges in execution, notably in the provision of adequate resources and teacher training. This research explores teachers' experiences with the program, highlighting the additional burdens placed on them, such as the personal cost of photocopying materials due to inadequate resources. It also discusses the program's lack of structure, training, and differentiation, as assessed by the Second Congressional Commission on Education (EDCOM 2). The study revealed themes in terms of teacher perspectives prior to the Catch-Up Friday program implementation, namely: educational impact, training and support, awareness and understanding. Moreover, three themes emerged for the challenges such as communication and coordination, teacher workload, and student engagement. Meanwhile, in terms of drawn insights, two themes appeared, namely: the importance of support and idealism and limitations. Furthermore, Theoretical frameworks such as Gardner's Theory of Multiple Intelligences, Organizational Theory, Cultural-Historical Activity Theory (CHAT), Resource Dependency Theory (RDT), and Complexity Theory provide insights into the complexities of implementing educational interventions. By examining these challenges, the study aims to propose solutions to improve the "Catch-Up Fridays" program's effectiveness and support its goal of leaving no student behind.