This paper is part of a dissertation exploring gender and family history in the Ottoman provincial city of Tripoli, in Modern day Lebanon, in the second half of the eighteenth century based on the sijjilat, the registers of the Ottoman Islamic sharia court. I started my research looking for women but kept bumping into children. In my quest for wives, mothers, sisters, daughters, or property owners, children and youth kept peeking their heads through the sources, boys more than girls, depending on the type of cases. In his work on Ottoman Tripoli, Beshara Doumani indicates that “the coastal cities [like Tripoli], it is presumed, are characterized by a modern nuclear family structure that put a premium on affective ties between husband/wife and parents/children.” In this paper, I look through the prism of the sijjilat and examine parents’ attitude toward their children in this nuclear family in terms of a dichotomy between affection and pragmatism. I argue that parents cared for their children and acted accordingly to ensure their wellbeing but mostly to secure their financial future. Though the children were ‘silent’ in the sources, they transpired as a social group that informs the debates revolving around childhood and parents/children’s relationships. I also show that there were nuanced indications that the court, symbolizing the Ottoman legal system, took every measure to ensure that adjudication took into consideration the children’s best interests. This paper also traces the interconnectedness between gender and childhood studies and the validity of conceptualizing the two fields as joint fields of inquiry. I show that children presented themselves as a category of historical analysis that is useful to better understand gender dynamics in an Ottoman milieu. The evidence from the registers shows that women’s agency transpires through matters related to children. Female Tripolitans, at least those who resorted to the judicial system to settle disputes, were clearly involved in the decision-making in matters related to their families, children, and other minor relatives. This paper also touches on the economic impact of religious endowments in Islamic societies. I look at this impact, that already got enough attention from scholars, from a different perspective related to the appointment of minor boys to waza’if (salaried jobs) within waqf establishments. Personal disputes cases (talaq, hadana, wisaya, nafaqa), cases of employment within waqfs, and property devolutions constitute the framework of this paper. I use Islamic sharia court registers, estates inventories, and fatawa collections.