As labor markets become increasingly global, competition among industrialized nations to attract highly skilled workers from abroad has intensified. Spurred by concerns over future economic needs caused by the demographic challenges of an aging population, both Japan and Sweden have joined this global competition. This article examines Japanese and Swedish immigration policies for highly skilled migrants and compares the highly skilled migrants' experiences in the two countries through interviews with these migrants. Despite Japan and Sweden's completely different approaches to immigration itself, both countries' policies, as well as the experiences of the skilled migrants, are strikingly similar. Highly skilled migrants experience language barriers and prejudice in both countries, making it difficult to build social networks with natives. Career development seems to be perceived as a common problem, although less so in Sweden, where labor markets are more flexible. Overall, these issues reduce both Japan's and Sweden's ability to retain skilled migrants. While they share similarities, Sweden's famed work-life balance and gender equality give it an edge in the competition for skilled migrants, which Japan does not share. This comparison identifies which social conditions facilitate or impede skilled migrant settlement.