The process of migration to a new country brings with it a host of challenges, and therefore also learning needs. Some countries have systems in place to facilitate the transition of migrants into society, often including adult education programs. Those programs, however, cannot be effective if blithely designed in ignorance of the interrelationship between established systems for facilitating integration and the experiences of migrants during the integration process. Focusing on the transition into the labor market and drawing on the expertise of adult educators who work in these systems in Germany, this article explores several stumbling blocks that make a successful integration for migrants more difficult and describes three strategies to address them: challenging the logic of the labor market, dealing with failure, and acknowledging multiple forms of discrimination. The analysis of Germany can provide insights that are useful in other national contexts.