School-to-work transition is a challenging period for youth with learning difficulties (LD). Based on self-determination theory (SDT), we tested the role of autonomy support and motivation in predicting transition status and well-being among this population. This prospective study included 218 students with LD in their last year of a work-study program. They were surveyed at the end of the school year and 1 year later. Two structural equation models were tested: one with the transition status as the outcome and one with well-being. Analyses revealed that autonomy support from fathers was positively associated with autonomous motivation in both models, as was autonomy support from friends in the transition status model. Autonomous motivation positively predicted both outcomes, while controlled motivation negatively predicted them. In sum, the psychological resources proposed by SDT seem to matter for youth with LD, thereby providing support for the generalizability of SDT.