For children who work, there has been little research into the intricate relationship between their home lives and their work lives and the implications that this relationship might hold for their psychosocial development and functioning. This cross-sectional study was conducted in the Amhara region, Ethiopia, between March and April 2020 on a sample of 1311 working children with the aim, in part, of exploring ways in which various dimensions of children’s psychological wellbeing are influenced by their working conditions and their family contexts. In addition to collecting data on some personal traits, family relationships, home environments, and detailed occupational characteristics, we gathered information on psychosocial wellbeing using 22 items from the Instrument for the Psychosocial Assessment of Working Children (IPAC). Exploratory factor analysis enabled us to identify five factors characterizing the dimensions of psychosocial wellbeing: work-related self-esteem, work-related stress, workplace supervision, emotional and somatic wellbeing, and self-determination. Linear regressions of these factors were then conducted on social, occupational, and environmental variables. We found that all dimensions of psychosocial wellbeing were significantly associated with the children’s working conditions. Of particular interest, work-related dimensions of wellbeing, such as stress, self-esteem, and supervision, were significantly associated with the characteristics of the home and family environment. These findings illustrate that work and working conditions must be considered jointly, along with family life and home environments, as factors in both environments affect working children’s socioemotional development and wellbeing. They also strengthen the call for a systemic approach to protecting children involved in child labor, in which families are central to all discussions.