Traditionally, Southern European countries displayed remarkably elderly biased social policy arrangements. This article introduces the notion of intergenerational recalibration to capture reforms aimed at rebalancing the generational profile of Southern European welfare states via the expansion of family policy and social assistance schemes—both monetary benefits and care services—and retrenchment in the field of pensions. Then, it elaborates theoretically on the political dimension of this policy strategy, focusing on the implications of the peculiar combination of expansionary and retrenchment reforms, to advance the hypotheses that domestic politics would prevent the realization of such an agenda, whereas the latter would be favored by a major role of supranational actors, especially the European Union. To test these hypotheses, we systematically analyze policy trajectories in the field of pensions and social assistance in Italy and Spain between the mid‐1990s and 2016. This allows, first, to argue that investment in “pro‐children” measures has not adequately balanced the reduction of pro‐parents expenditure and, second, to question the idea that domestic political incentives to expand “pro‐children” policies are necessarily too weak as well as the “enabling” role of external pressures in pursuing intergenerational recalibration.