Economic and technological change has made lifelong learning more important than ever and partly explains the rise of online education, the flexibility of which appeals to mid-career Americans. Most existing online education appears to result, however, in poor learning and labor market outcomes. Promising models of low- cost, high-quality online education are only now beginning to arise. This chapter lays out some of the central questions policymakers should ask when considering plans to leverage online education for economically vulnerable mid-career Americans, as well as the state of the evidence surrounding those questions. In short, existing research provides little clear evidence of successful models of online education for academically weaker students, suggesting that policymakers should proceed with caution. Any such efforts should be accompanied by rigorous, data-driven assessment and accountability systems, both to encourage pedagogical innovation and to ensure students benefit from such degrees.