Work-based learning experiences (WBLEs) are an important part of vocational programming for students with extensive support needs (ESN); however, the development and implementation of these experiences can present challenges for special education teachers. The purpose of this qualitative study was to explore the challenges that special education teachers face when providing WBLEs for transition-age students with ESN. Nine special education teachers were identified through purposeful sampling methods. Participants met the following inclusion criteria: (a) teach students aged 14 to 22, (b) serve primarily students with ESN, (c) have 3 or more years of experience teaching 14- to 22-year-old students with ESN, and (d) be actively involved in planning and implementing WBLEs for 14- to 22-year-old students with ESN. Data were collected through semi-structured interviews and analyzed using thematic analysis. Findings from this study suggest that special education teachers face many diverse challenges when providing WBLEs to students with ESN, including establishing and sustaining appropriate WBLEs, securing high-quality staff, gaining support of important partners, and navigating logistics. Findings from this study have practical implications for supporting special education teachers who provide WBLEs for students with ESN. Findings also highlight the importance of improving attitudes and perceptions around employment outcomes for students with ESN.