Occupational welfare as an alternative to public welfare for the protection against social risks has lately attracted increased attention. However, there is no clear agreement on the causes behind the emergence and expansion of occupational welfare schemes in modern welfare states. This article contributes to this subject through a study of one specific form of occupational welfare in Sweden, called Employment Security or Transition Agreements, and the agreements between the bargaining cartel for white-collar employees PTK and the Confederation of private-sector employers SAF/SN from the 1970s until the present time. Based on archival material and articles, the article finds that the protection provided through the agreement expanded during the 1970s and 1980s but has since been reduced, even though the unions finding such solutions more important than ever. Despite the relative strength of Swedish unions, they are not able to sufficiently address increased labor market risks brought about by welfare state retrenchment and structural change.