Secondary educators implement an array of work-based learning activities that expose transition-age students to the demands of post-secondary employment. One such strategy, internships, provides students with a formal opportunity to acquire transferable employment skills that lead to meaningful post-secondary employment outcomes. Facilitating internships for transition-aged students with disabilities, however, presents challenges for educators because internships often involve complicated and sometimes ambiguous labor laws, regulations, and provisions. This article provides secondary educators with information about how to facilitate unpaid and paid internships for students with disabilities that align with requirements established by the Fair Labor Standards Act. The article provides a case study to illustrate how schools can develop both unpaid and paid internships and concludes with recommendations for best practices.