This chapter provides an analysis of school-to-work transitions in five Arab Mediterranean countries: Algeria, Egypt, Lebanon, Morocco and Tunisia. Transition processes in these countries are shaped by strict cultural norms such as the central role of marriage, labour market segmentation and demographic changes, which put tremendous pressure on educational systems and labour markets. Using quantitative and qualitative data from the SAHWA Youth Survey 2016 (2017) and the SAHWA Ethnographic Fieldwork 2015, special attention is paid to the effect of gender, social origin, place of residence and education on the career opportunities of young adults. The chapter concludes that the transition from school to work poses a major problem in most Arab Mediterranean countries. While the correlation between rural and urban employment is low, young women’s labour market participation rates are much lower than those of their male peers. Additionally, in all countries but Egypt, the level of education is positively correlated with an increase in young people’s job opportunities. The results obtained show that institutional quality shapes young people’s trajectories in various ways and points to the need for further policy action.