This article explains the dilemmas facing Japan and the United States in undertaking immigration policy reform. For the Japanese, the main dilemma is how to confront the inevitable consequences of a rapidly aging population and declining workforce on Japan’s ability to maintain its competitive edge in the global market and to sustain its social security system without increasing immigration, which is still viewed by many as socially disruptive. The U.S. immigration dilemma is of a totally different nature, since it is about a broken migration system that continues to produce half a million undocumented migrants every year. On one hand, granting amnesty or an easy path to regularization to millions already in the country via irregular means is widely seen to be unfair and a strategy that will only undermine the established procedures for legal admissions. On the other hand, mass expatriation is not an option since labor shortages are still experienced by many American industries even at the height of unemployment. Moreover, the continued employment of Mexican migrants is important to Mexico’s economic development, which in the end is the key to solving the U.S. dilemma.