A host of challenges have been associated with providing work-based learning experiences (WBLEs) for students with disabilities; however, little is known about how special education teachers navigate or overcome these challenges. The purpose of this qualitative study therefore was to understand how special education teachers respond to the challenges they experience when providing WBLEs for students with extensive support needs. Participants were nine special education teachers in a Midwestern U.S. state who primarily serve 14- to 22-year-old students with extensive support needs. Each teacher participated in one semi-structured interview, and transcripts were analyzed using thematic analysis. Teachers reported responding to challenges by (a) creating authentic school-based work experiences, (b) providing direct support for students and families, (c) networking and building new connections, and (d) advocating for students in school and community contexts. Findings from this study have practical implications for special education teachers who provide WBLEs for students with extensive support needs.