Nearly 175, 000 Haitian immigrants have settled in South Florida since the 1970s. Their lives are often lived transnationally with persistent connections and obligations to family members in Haiti. Yet, traditional theories of immigrant assimilation focus on the integration of immigrants into host countries, giving little consideration to relationships and activities that extend into migrants' countries of origin. Conversely, studies of transnational families do not explicitly address incorporation into the receiving country. This dissertation, through the experiences of Haitian immigrants in South Florida, reveals a transnational quest “to raise the family up” through migration, remittances, and the pursuit of higher levels of education. I argue that familial duties and obligations, which have cultural foundations in the Haitian lakou, structure the activities of Haitian transnational families as they pursue socioeconomic advancement through migration and education. With the support of transnational families, many students cross boundaries to academic achievement and improve their opportunities for socioeconomic mobility in the US. With higher levels of education, these individuals contributed to a more favorable incorporation into the United States for their extended families, as well. The data were collected through participant observation and 78 in-depth interviews documenting the migration histories of 27 Haitian immigrant families in South Florida. This dissertation contributes to the existing literature on Haitian immigrants in the United States and to an understanding of the transnational dimensions of immigrant incorporation more broadly.