How have immediate school-to-work transitions and early careers changed in different labor market entry regimes since the early 1980s? How do institutional frameworks differ with regard to insecurity perception? This book investigates these topics from a cross-national perspective while focusing on Denmark, the darling of flexicurity literature. The results show that in all the labor market entry regimes, the school-to-work transition has become increasingly difficult, and flexible forms of work are more typical in the first job. Furthermore, the liberal institutional framework of the United States seems to produce a similarly low degree of job-loss worry among young people in their early careers as does the Danish paradigm. Contents include: employment flexibilization and increasing economic insecurity at labor market entry * the role of institutional settings for shaping school-to-work transitions * the Danish flexicurity as a framework for labor market entry processes * insecurity experiences: the development of employment risks at labor market entry since the 1980s * insecurity perception: the translation of unemployment risks into job-loss worry in times of flexible employment.