This chapter adopts a dynamic approach to the study of youth labor market integration. It focuses on individual trajectories (i.e., sequences of employment statuses) and considers the timing, order, and length of employment and jobless spells. It uses EU-SILC longitudinal data (2006–2012) for 17 countries to depict youth employment outcomes in two different phases: labor market entry and approximately 5 years after leaving education. The extent to which the experience of a certain trajectory type differs by gender, education level, and across countries is analyzed. Results show that although males and females have similar chances of accessing paid employment rapidly, women’s labor market conditions deteriorate over the following few years in terms of both security and success. Stricter rules on the use of temporary contracts tend to reduce the probability of fragmented trajectories in both phases, narrowing the gender and education gaps with respect to employment and income security.