This study investigated caregiver-initiated contacts to a statewide, phone-based adoption support program to understand the breadth and range of challenges families experienced during the post-adoption period. Characteristics of families and their reasons for seeking post-adoption support are described, and the relationship between family characteristics and the type and range of challenges families reported were examined using bivariate and multiple regression analyses. In one-year caregivers from 238 families representing 257 adopted children sought phone-based post-adoption support. Callers had primarily adopted children internationally or from U.S. child welfare systems. The average child age at the time of adoption was 3.6 years, however post-adoption help seeking occurred when the average child age was 12 years. Caregivers reported an average of 9 different challenges which crossed four domains; child emotional-behavioral difficulties, caregiver strain, school challenges, and adoption specific resource and assistance needs. Challenges were positively correlated and co-occurring. Larger sibling groups were associated with increased child behavior issues, caregiver strain, and school related challenges. Older sibling groups and adoptions from foster care were associated with increased school related challenges. The timing of caregiver help seeking suggests the transition from childhood to adolescence may be a particularly vulnerable period for some adoptive families, and post-adoption service providers should consider bolstering supports for adoptive families during this time. The breadth and range of challenges reported also suggest the need to increase the availability of multidimensional, adoption-specific services for children, caregivers, and broader family system in the years following adoption finalization.