After several decades’ hiatus, there has been a sustained surge of Chinese emigration and resurgent opportunities for transnational activity since 1978. In this paper, we engage with the burgeoning literature on transnationalism, focusing on the roles of immigrant agency, disaporic communities, and nation states to examine the means and consequences of diasporahomel and interactions in different host societies. Specifically, we address the following questions: (1) How do emigration histories and receiving contexts matter in shaping diasporic formation? (2) Who is involved in diaspora-homeland interactions and what roles do different actors play? (3) What bearing do immigrants’ transnational engagements have on their hostland integration? Through a comparative analysis of contemporary Chinese immigration to Singapore and the United States, we examine the interrelations among different actors and the roles each plays in cross-border activities. We find that differences in emigration histories and receiving contexts affect diasporic formation. We also find that immigrants maintain ties to their homeland, or sending state governments reach out to expatriates, through diasporic communities despite differences in diasporic formation. Moreover, varied levels of diaspora integration into the receiving countries affect how receiving states respond to immigrant transnationalism. Finally, we discuss the implications of homeland-diaspora interactions, showing that transnationalism is utilized by new Chinese immigrants as an alternative means to socioeconomic status attainment and that it facilitates, rather than hinders, immigrant integration into host societies.