This qualitative phenomenological study explored the lived experiences of kindergarten teachers in implementing contextual performance assessment in Sto. Tomas East District, Davao del Norte. The researcher selected ten participants through purposive sampling and gathered data using in-depth interviews and focus group discussions guided by a semi-structured interview guide. Findings revealed that teachers embedded real-life skills in assessments by integrating home-based tasks and encouraging learner independence. However, they faced challenges such as limited materials, time constraints, and inconsistent understanding of contextual assessment. Despite these barriers, teachers observed increased engagement, better retention, and improved confidence among learners. To cope, they engaged in professional growth, used humor, and applied resourceful strategies like DIY materials and digital tools. They also drew strength from administrative support, collaboration with parents and peers, and structured feedback systems. These insights underline the importance of leadership, community involvement, and continuous monitoring in sustaining meaningful assessment. The study implies that aligning assessments with children’s real-life experiences and supporting teachers through training and resources enhances implementation. This research provides a valuable foundation for improving early childhood assessment practices.