Assessment of the caregiver-child relationship has become an intrinsic part of the preschool child psychiatric evaluation. Normal and abnormal development of relationship is influenced by a myriad of genetic, psychological, cultural, and environmental factors in both the caregiver and the young child. In the past, professionals from different fields, like pediatrics, neurology, development, and social welfare, would understand the child and his or her environment with their own tools. Since then, these parallel lines have converged into a more complementary and integrated view. The need to evaluate the caregiver, the child, the caregiver-child interaction, and the context of the relationship makes the evaluation a challenging multidisciplinary process, in which standardized assessment tools have to be integrated into a sound clinical conceptualization of the evaluated relationship.