The aim of this study was to assess the primary concerns of parents/caregivers regarding their young child's sleep. A total of 1,287 consecutive sleep-related questions were analyzed from submissions to an Ask the Expert section of a publicly available iPhone-based application for sleep in young children. Questions regarding infants were most likely to be submitted (53.9%), followed by newborns (23.76%) and toddlers (17.8%), with an average age of 10.94 months. The primary concerns regarded night wakings, sleep schedules, and bedtime problems, accounting for almost 85% of all questions. Results align with common concerns noted in epidemiological studies. Understanding the types of concerns for which parents seek advice is beneficial in the continued development of resources for caregivers.