The objective of this article is to investigate how psychosocial difficulties, functional level and school factors affect social security dependence among former students with special needs (N = 373). These individuals have been followed prospectively from their teens and into their late twenties. The study is theoretically inspired by life-course perspectives, with emphases on transitions, linked lives, geographical and historical location and human agency. More than one-third of the study participants are dependent on social security. The logistic regression analyses show how each of the seven independent variables--while simultaneously controlling for the other covariates--impacts adult adaptation to social security. Women have almost a threefold higher risk of social security dependence than men. The covariates affect males and females differently. For men, the risk is especially high if they have psychosocial problems, are supported by teaching assistants in class or experienced delayed educational transitions. For women, the risk is elevated if their functional level is low or school results are poor.