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Definition: This entry delves into the parenting literature and reveals the complexities, perspectives, and multiple expressions of parenting challenging childhood behavior that distress or negatively impact the parent-child relationship so that we can better understand how to support families who are struggling to cope. The entry specifically focuses on the period of transition to school for children aged five to eight years. This transition can illuminate vulnerabilities previously hidden as children attempt to navigate the demands of their unfamiliar environment, meaning that parents can experience distress and emotional challenges. The entry explores the various expressions of relationally challenging behavior and comments on the intersectionality and reciprocity of explicit and implicit expressions of affect such as frustration and anxiety. To gain context, the entry examines common antecedents associated with relationally challenging behavior, such as academic comparison, forming friendships, hidden neurodiverse development, neglect, attachment dysfunction, and family conflict. Qualitative literature enriches understanding and identifies problems such as parental distress related to social stigma and minority stress and reveals specific struggles, including stress, related to homeschooling children with special educational needs, homeschooling during the recent pandemic, single parenting, grandparenting, parenting neurodiverse children, and the triangulated tensions that exist between the parent, the child, and the school. Holding in mind these diverse and context-orientated perspectives, this entry examines research that evaluates helpfulness and illuminates deficiencies of popular structured parent programs. Lastly, the entry identifies and illuminates the need to know more about the ways in which parent programs work, and it is anticipated that this new knowledge will help practitioners to better respond to the complexities of need and expectations of families who struggle to cope with relationally challenging behavior. [ABSTRACT FROM AUTHOR]