This study explored the perspectives of Grade One teachers on the transition of learners from kindergarten to Grade One. Ten (10) Grade One teachers from Governor Generoso-North District, Division of Davao Oriental, participated in the research. Employing a phenomenological approach, the study gathered in-depth insights through individual interviews and focus group discussions to uncover their experiences, coping mechanisms, and reflections. Thematic analysis revealed key themes related to their experiences, including academic transition, social-emotional readiness, and teacher professional development. In addressing challenges, the teachers employed strategies categorized under three themes: emotional regulation and stress management, collaborative planning, and strategic organization. Insights generated from the study included the integration of social-emotional learning into curriculum and instruction, implementation of play-based learning, continuity between Kindergarten and Grade One, and data-driven decision-making alongside sustained professional development. The findings underscore the critical influence of effective transition practices on learners’ early academic success, particularly in literacy, emotional well-being, and adjustment to structured learning environments.