This article describes an overview of key findings from the Comparative Welfare Entitlements Project (CWEP). CWEP compiles major features of the generosity of unemployment, sickness and public pension programs over the last several decades in 21 countries. Describing and extending earlier work to measure the institutional variation in major social insurance programs over time, we provide previously unpublished methodological details of widely used measures of program generosity; measures which have appeared in over 200 analyses during the last decade and a half. We find a high level of variation in wage replacement and benefit conditionality across programs in most countries; calling into question the notion of an historically stable configurations of characteristics, at least during the last 45 years. For instance, our research shows that several prototypical social democratic welfare states experienced the highest declines in generosity in the last three decades. Furthermore, we also show that, as late as the mid‐1970s, some ‘social democratic’ welfare states still trailed some ‘conservative’ welfare states, including prototypical ones like Germany.