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Despite considerable interest in promoting children’s cognitive readiness for school, kindergarten transition difficulties can hinder skill development during kindergarten, leading to longer-term under-achievement. This study investigated the role of children’s (n = 626) kindergarten transition difficulties and their development in academic and social skills during the kindergarten year. Results from a series of covariate-adjusted regression models showed that children who experienced more transition difficulties at kindergarten-entry demonstrated relatively fewer gains in math, reading, and social skills across the year, even when controlling for kindergarten-entry skills. The findings indicate that kindergarten transition difficulties function independently from initial academic and social-behavioral skills on children’s development in the kindergarten context and signal the value of research on the construct of kindergarten transition difficulties.