Since the end of the Cold War, developed countries have tried to increase their intake of highly educated immigrants. Simultaneously, there has been exponential growth in the number of foreign students who come to developed countries for university degrees. Many countries have linked these two phenomena through “talent retention strategies,” which are policies that allow international students to apply for permanent immigration status. Though employers and universities in the United States have actively lobbied for such policies in the last two decades, they have consistently failed to come to fruition. Canada, on the other hand, is often regarded as a world leader in talent retention and a model for other countries to follow. Why did talent retention strategies succeed in Canada but fail in the United States? Using comparative-historical methods, I examine the development of immigration preferences for international students in the two countries. I find that they treated immigrants similarly in the 1800s and early 1900s. In the 1960s, they faced international and domestic pressures to remove racial discrimination from the immigration system, but came up with very different reforms in response. Canada prioritized highly educated migrants, used guestworker programs to address demand for low-skilled labor, and gave the federal executive branch and provincial governments leeway to experiment with immigrant selection. The United States prioritized family migrants, left low-skilled migration unaddressed, and centralized all immigration rule-making in the fractious federal legislature. These differences shaped the political opportunity structure in later decades. While conditions in Canada facilitated the introduction of talent retention strategies there in the 2000s, circumstances in the United States stymied similar proposals. This study contributes to the immigration policymaking literature by showing how historically-specific constellations of interests and institutions can obstruct the passage of immigration provisions that are broadly popular among key constituencies. This dissertation also challenges the reader to consider how immigrant selection policies may impact other policy areas, including higher education, science and innovation, and foreign relations.