The threads of a new vision for the transition from prison to work are present in what is known about the employment-related needs of prisoners, the current opportunities and restrictions on work in prisons, the concerns of potential employers, and the essential elements of the handful of programs that have shown promising postrelease employment outcomes. The challenge remains to weave these threads together into an integrated whole, one that maximizes the opportunities for learning, experience, and skill-building that is present during incarceration, featuring a seamless transition to work beyond the prison walls. The fifth in a series of Reentry Roundtable discussions was held in May, 2003; the result of which included several papers and presentations forming the conceptual framework of this report. The aim of the report is to highlight relevant research and identify key policy issues. The report first addresses the relationship between work and reentry, outlining the links between gainful employment and individual, familial, community, and societal outcomes once prisoners are on the outside. Next, it describes the current labor market, identifying the gap that former prisoners could potentially fill when they enter or return to the work force. The focus then shifts to explore the skill sets, education levels, work histories, and health-related needs of returning prisoners. The report examines the past and current state of work inside State and Federal prisons. The report looks at the opportunities for, as well as the legal barriers to work on the outside, drawing on lessons learned from three effective employment programs. The report concludes by identifying key considerations to meet the goals of enhancing work opportunities available to prisoners and expanding work opportunities after release. Figures, references