This phenomenological study was conducted primarily to determine the lived experiences of kindergarten teachers on administering classroom assessment. Seven (7) teachers were included as participants of this study and were selected using purposive sampling. The researcher-made interview guide was utilized to capture the responses of the participants through the conduct of Face-to-Face Interview. The study highlights the importance of assessing children in school, ensuring interactive assessments to stimulate early-year learners' playful nature, and fostering patience and understanding to promote a healthy learning environment. It also highlights the role of diversity in modern education, allowing teachers to develop their creativity in creating meaningful and authentic learning materials for different learning preferences. Furthermore, participants believed that assessment is a critical component to classroom learning and helps guide decisions surrounding curriculum, instruction, and individualization hence, inability of the pupils to participate in assessment not only compromised the objectives assigned to the tasked but the totality of the purpose of the assessment. Teachers expressed concerns about an unreliable testing tool with a low percentage margin of errors, recommending a full review and revision of the assessment tool. Participants used various coping mechanisms to prevent negative progress in their problems, including remediation activities, rewards, superwoman status, interactive learning, and technology-based learning. These strategies were effective, positively influencing learners' attitudes towards learning and post-test performance. This only suggests the implication of differentiated activities as intervention to the learning and assessment of learning were quite beneficial.