Background: Research indicates that transition-age youth with disabilities face several obstacles with regard to finding employment. However, research on the extent to which barriers and facilitators differ across disability types and contexts is lacking. Objective: The primary purpose of this qualitative study was to understand employment-related challenges encountered by a cross-section of transition-age youth with disabilities across multiple settings. In addition, the study also examined transition-aged youth's knowledge and use of rights under the Americans with Disabilities Act (ADA). Methods: We adopted a focus group strategy to understand the barriers faced by transition-aged youth with disabilities; five focus groups were conducted at five community-based locations in three states (Maryland, Delaware, and Virginia) in Federal Region 3 (i.e., Mid-Atlantic). Participants ranged in age from 16 to 24 (53.5% male; 44.2% White). Findings: Findings indicated that youth with disabilities faced several barriers in the form of stigma, lack of workplace supports and accommodations, their disability condition, and anxiety. In addition, a very small proportion of the sample were aware about the ADA and their rights under Title I. Conclusions: Findings highlight the need to develop programs that equip transition-aged youth with disabilities with the necessary skills as they prepare to enter the work force. In addition, efforts should be targeted at addressing the barriers identified in the study, such as stigma, as well as at increase students' knowledge of the ADA by embedding information within secondary and postsecondary academic curricula.