This dissertation broadens the theoretical focus of transnationalism and remittances to include that of the second generation via brokered social ties. In particular, I focus in expanding the theoretical scope of the New Economics of Labor Migration by discussing how migrants actively facilitate the second generation within transnational household financial decisions with nonmigrants in the ancestral home country. In so doing, this dissertation outlines the ways in which second generation cross-border ties are uniquely constructed and sustained in a manner that is different from that of first generation connections, both logistically and relationally. Throughout the first of half of the dissertation, the case of second generation Mexican and Filipino Americans remittances are used to illustrate the ways in which brokerage is centrally required to mediate both cross-border connections and financial remittances generally. By examining second generation Mexican- and Filipino-Americans, two groups that differ in linguistic proficiency, geographical proximity to the home country, and interpersonal contact with nonmigrants, this dissertation highlights the common role of a broker for both groups. Building on this theoretical expansion, this study illustrates the importance of social and familial relationships on a generalizable level by testing hypotheses derived from transnational scholarship to prove that the decision to remit among the second generation is shaped on a household-level, both financially and socially with household decisions manifesting uniquely within particular remittance corridors. Finally, this dissertation concludes by examining the differential effects that factors have on first and second generation remittance practices. In so doing, this final section demonstrates how the first and second generation fulfill different financial roles within a remitting relationship. In addition, effects are not uniform in how they affect the differences in the likelihood of remitting and the average amount of money sent in each transfer across generations. As the second generation are much more rooted in their country of birth, aspects of social connections with those in the ancestral home country shape the likelihood of remitting and the average amount of money sent in each transfer in a different manner compared to the first generation.