Work-based learning experiences (WBLEs) provide students with opportunities to learn about careers and gain work skills required for post-school employment. WBLEs may be especially important for students with extensive support needs (ESN) who often struggle to access competitive, integrated employment after graduation. The purpose of this study was to understand teachers' beliefs about the benefits of and barriers to school and community WBLEs for students with ESN. We invited 1,498 U.S. special education teachers with a license in ESN to participate. Eligibility criteria required teachers to have at least one high school student with ESN on their caseload. Of the 273 teachers who responded, 137 met criteria and completed the questionnaire. We used descriptive statistics, exploratory factor analyses, and nonparametric inferential statistics to analyze our data. Teachers believed students benefit from WBLEs because they learn skills and have improved outcomes; however, they rated student outcomes higher for community WBLEs (vs. school WBLEs). Barriers to WBLEs included limited resources, stakeholder support, curriculum, and support for students. Teachers rated barriers related to stakeholder support and support for students higher for community WBLEs (vs. school WBLEs). Teachers' beliefs about the benefits of and barriers to WBLEs varied by their experience with WBLEs. Implications for future research about students' experiences during WBLEs and how teachers make decisions about WBLEs are discussed.