This article analyses practices of intergenerational support for homeownership among different generations of families in Milan, Italy, highlighting the role of housing in family welfare relations and life-course transitions. It makes use of an original dataset of qualitative interviews investigating homeownership pathways and the negotiations of support that they pre-suppose. The article explores the meanings and moral reasoning behind the decision to accept (or not) support in context of contemporary discourses surrounding the liquidity and availability of housing and finance. It highlights the moral compromises and emotional negotiations inherent in the giving and receiving of support for housing, contributing to a body of literature concerned with the reproduction of home and family. Furthermore, it stresses the importance of homes and housing assets in mediating dependence and re-affirming family bonds within a family-oriented welfare context, despite conflict, resistance and frustrated aspirations.