This research examines the implementation of DepEd Catch-Up Friday, a strategic initiative introduced by the Department of Education in the Philippines to address academic disruptions caused by the pandemic. The study investigates how this initiative has affected teachers’ practices, workload, and overall well-being. A qualitative study, particularly phenomenological inquiry, was used. Through purposive sampling, 22 secondary public-school teachers served as participants in this phenomenological study. The results yielded three themes with regard to the experiences in Catch-Up Friday: challenges in the preparation, gaps in educational resources, and barriers in student motivation. Regarding the coping mechanisms of teachers in Catch-Up Fridays, four themes emerged: strategic intervention, diverse expertise, systematic evaluation, and technology-enhanced instruction. Moreover, three themes emerged as the insights of teachers in the implementation of Catch-Up Fridays: an inclusive learning environment, addressing struggling learners, and requiring tailored instructional approaches. Recommendations include strengthening support structures for teachers, promoting student-centered approaches, and implementing structured feedback mechanisms to continuously improve the initiative. The research underscores the need for ongoing evaluation and adjustments to ensure that DepEd Catch-Up Friday effectively supports students and educators, fostering a more resilient and adaptive educational environment.