The economic crisis has highlighted major shortcomings in the EU flexicurity strategy which, although suitable to tackle structural unemployment in a period of economic growth, it proved unable to stand the impact of the recession, which requires specific measures to maintain employment. Against this background, the authors of the present papers, which were presented at the International Scientific Conference “Labour Market of the 21st Century: Looking for Flexibility and Security”, on the occasion of the 370th Anniversary of the establishment of Vilnius University’s Faculty of Law, that took place on 12–14 May 2011, investigate the development of labour regulation in the 21st century, with particular reference to the relation between flexibility and security and to the need to strike a balance between these two elements. The contributions address the issue in a comparative and transnational perspective and provide some insights into the development of national models of flexibility and social security.