Despite the recent success of the Temporary Assistance for Needy Families (TANF) program in reducing caseloads and moving a large share of former welfare recipients into work, there are lingering concerns that some families may encounter substantial difficulties achieving independence from cash assistance. This study uses administrative and survey data to profile the District of Columbia's TANF caseload in August 2002--approximately five years after the implementation of welfare reform. It examines the challenges DC's welfare recipients face as they try to move from welfare to work, the extent to which they do work despite these challenges, and differences between subgroups of welfare clients.