A key stage in early life education, the change to kindergarten shapes a child’s cognitive, social, and emotional growth. This study investigates parents’ actual experiences choosing kindergartens and helping their children to transition. Structured interviews with 21 parents using a phenomenological research design helped to provide an in-depth understanding of their emotions, difficulties, and techniques during this process. Findings show that parents go through excitement, pride, worry, and concern mixed with important obstacles such as separation anxiety, socializing difficulties, and adaptation to school routines. Among the elements that helped to ensure a seamless transition were parental planning, school orientation programs, teacher assistance, and honest communication between parents and teachers. To help their children adjust, parents used storytelling, role-playing, and daily routines, among other techniques. To make the kindergarten experience better, the study underlines the need for structured transition programs, improved school-parent communication, and more emotional support systems. Among the recommendations are strengthening parental involvement, running orientation programs, teaching instructors in transition support, and funding early childhood education. Children’s kindergarten experiences can be more seamless and positive by means of cooperation among parents, teachers, and legislators, therefore laying a strong basis for lifetime learning.