<p>As China expands childcare provisions for children under three, a growing number of toddlers are entering kindergartens that traditionally served 3- to 6-year-olds. This study investigates the challenges and strategies associated with such transitions through a case study conducted in a toddler class in eastern China. Drawing on interviews, non-participatory observations, and document analysis, the study identifies three major challenges—teachers’ limited experience in toddler care, low adult-child ratios, and parental anxiety—and five supportive strategies ranging from increasing the adult-child ratio to using visual cues and multimedia. Notably, teachers frequently used distraction techniques but rarely employed reappraisal to directly address children’s emotions. Screen-based multimedia, including cartoons and video games, were also used to support children’s adaptation. While parent-teacher partnerships were emphasized, parental involvement remained largely limited to information exchange and home-based support. This study offers a concrete example of how toddler transitions are organized in a Confucian-influenced society, contributing to global understandings of cultural variation in early childhood transition practices. The findings have significant implications for both policy and practice, especially in light of the Chinese government’s recent push to integrate care and education for children aged 0–6 and to expand access to high-quality, affordable childcare as part of broader demographic strategies.</p>