Age-related regression of the thymus is associated with a decline in naïve T cell output which is thought to contribute to the reduction in T cell diversity in older individuals that is partially responsible for an increase in susceptibility and severity of infections, cancers and autoimmune diseases. Thymic involution is one of the most dramatic and ubiquitous changes in the ageing immune system, but the precise regulators remain anonymous. However, a picture is emerging, implicating extrinsic and intrinsic factors that may contribute towards age-associated thymic involution. In this review we assess the role of the thymic microenvironment as a possible target of thymic involution, question whether thymocyte development in the aged thymus is functional and explore why the thymus involutes.