This Article reviews the relationship between U.S. policy after the 1959 Cuban Revolution and the legal mechanisms that have influenced the character of the binational Cuban-American family since then. Over the course of the last fifty years, the United States has used the rule of law to deny families fundamental customs of care-taking and comfort. Of course, the immigration regulations and attendant matters of travel and remittances are customarily linked to national policy and international concerns. However, in the case of U.S. laws governing the relationship of Cuban binational families, there is no normativity of impartiality that can be discerned, a condition that continues notwithstanding some recent changes announced by the Obama administration. These efforts have failed to achieve their goals. Cuban-American families have improvised—often extralegal—mechanisms of familial support. In doing so, they act as transgressors of laws and policies as a means to maintain family support systems.