The present study utilised naturalistic observation to assess the impact of parental departure during daily drop-off at preschool on children's settling into daily preschool routines. Forty-six 3-5-year-old children and their parents/caregivers were observed during morning drop-off at preschool. Longer latencies of parent/caregiver leaving were associated with less child-peer engagement, solitary active play, and onlooking and were associated with more child-caregiver proximity-seeking, hugging and kissing, and picking up and holding. Mothers and other female caregivers were slightly more likely to pick up and hold their children during drop-off than fathers and other male caregivers. Findings suggest that continued parental involvement may initially hinder children's daily settling into the preschool classroom environment through facilitation of escape or avoidance. Additional research is needed to better understand individual differences that may serve as protective factors or vulnerabilities affecting children's daily adaptation to the preschool environment.