This paper answers these questions about the challenges welfare-to-work programs face as more of their Aid to Families with Dependent Children (AFDC) caseload becomes subject to work requirements: (1) What challenges will hinder a welfare recipient's move into employment? (2) What is known about the prevalence of barriers to employment? (3) When the presence of multiple barriers is considered, what fraction of the AFDC caseload is likely to experience at least one barrier to employment? (4) What is known about the relationship between work barriers and work experience? (5) What are the implications for designing and delivering welfare-to-work programs?