The integration of long-term unemployed individuals into the labor market is a key objective of modern social policy in Germany. Activation and the associated conditionality of social benefits have important implications for the perception of the unemployed, who are increasingly exposed to stigmatization. Moreover, health problems and disabilities constitute the primary rationales for a (temporary) limited employability assessment among these groups, which allows individuals to receive unemployment benefits while being exempt from the obligation to look for a job. The medicalization of unemployment might therefore constitute a legitimization of this status, diminishing social stigma. In this article, we investigate whether a medical leave status reduces the perceived stigmatization among those groups. Using entropy balanced OLS-regressions with data from the “Labor Market and Social Security Panel” (PASS), we find no significantly lower stigma for unemployed persons on medical leave.