Examining the generosity of welfare states and individual benefit schemes is a classical task in comparative welfare state studies. Three types of welfare states can be discerned based, in part, on their level of benefit generosity. Although significant advances have been made in the development of measures of welfare state generosity, this progress has not been without its challenges and limitations. In this article, the authors examine two sets of limitations related to measurement validity in comparative welfare state research: securing content validation and ensuring comparability across time and place. Through the use of illustrative examples to compare the situation of the unemployed in five European countries across several income levels and two family types, we demonstrate that, by profiling and stacking public benefits using the OECD Tax-Benefit micro-simulation model, we are able to carry out a more informed analysis of the redistributive strategies of the welfare state.