Drawing on qualitative interview data, this article examines how grandfatherhood relates to the assertion and transformation of masculinities in later life. Recent attention to ageing and masculinities has identified how older men are challenged to succeed in maintaining connections to hegemonic masculinity in light of altered family and life circumstances. We consider men’s engagement with grandfatherhood as a means for so doing, illustrating how men make sense of the role through continuity with hegemonic masculinity. While grandfathers describe emotionally intimate and affectionate relationships with their grandchildren, their accounts reflect desires to re-affirm previous connections to masculinities. Attention to the way individualised masculinities are re-negotiated in later life can help to explain how men are making sense of the new family opportunities that arise from being a grandparent. Such an analysis of grandfatherhood, we argue, also offers significant critique of hegemonic masculinity and its distinction to non-hegemonic masculinities intersected by old age.