This article examines pathways to intergenerational transmission of gender values, norms and ideology with a particular focus on contexts where there is a strong intersection between gender and poverty. The first part explores the multiplicity of conduits of knowledge and influence across generations. The potential for reversing the direction of intergenerational influence and challenging its unilinearity are further examined in a study of a project supporting child leaders in Egypt. The article explores the opportunities and challenges in facilitating children's agency in poor communities and argues that although they were able to challenge social values on various levels, their agency was limited by structural factors. The last section examines some of the structural dynamics associated with the demise of the gender contract (in practice but not in ideology) on intergenerational transmission of values and ideas, and how they may bring possibilities for disruptions in gender ideas and values, both positive and negative.