This paper analyzes in-depth interviews with 45 frontline welfare workers and clients in one county to explore the perceptions that develop at the front-lines of the welfare system and to consider how these perceptions may influence new welfare reform strategies. This exploratory study finds that welfare workers utilize three distinct typologies to understand their clients. In contrast, clients believe that the welfare system is not designed to help them succeed, that many workers are personally invested in enforcing system rules, and that administrative policy is inconsistently applied. While both workers and clients believe that the new policy goal of employment is important, they both raise considerable questions about the barriers and disincentives that many clients may encounter as they try to leave welfare for work. This paper concludes by considering how these conditions may influence implementation of the most recent round of initiatives to reform the welfare system. (author abstract)