Having a job, or being employed, is associated with a number of positive effects. Although policies in Sweden support the right of people with disabilities to work and highlight access to employment as a priority, this group of people continues to lose out in employment against other citizens. However, little is known about actions or initiatives implemented to enhance labor market participation among people with disabilities. This study contributes useful findings on a promising implementation of a school-to-work transition initiative, workplace based learning (WBL), in special needs upper-secondary schools in Sweden. The aim of the study was to identify how teachers, having a key role in the implementation process, view and experience WBL and its actual functioning to enhance school-to-work transitions for students with intellectual disabilities. Drawing on 13 interviews with teachers working as supervisors and coordinators in the WBL training, our findings lead to three main conclusions. First, the teachers had significant reliance on WBL and its potential to prepare students for the labor market. Second, the teachers hesitated with regard to whether and to what extent WBL actually enhances school-to-work transitions. Third, the WBL reform has had significant negative effects on the working conditions of the supervising teachers involved. Our study uncovers a number of barriers for WBL to function as an actual bridge to work for students with intellectual disabilities, which we argue have important messages to bring for both policy and practice.