Singapore currently faces the dual demographic problem of low birth-rates and a rapidly ageing population, which results in a productive population deficit in all categories of labour and necessitates an unavoidable dependency on foreign labour. Indians migrate to the city-state responding to this contemporary demand for labour and for reasons ranging from centuries-old migration pathways, an established ethnic infrastructure, and geographical proximity to the better livelihood opportunities the global Singaporean economy offers. The various phases of Indian immigration to Singapore since the pre-colonial times have caused the disparate development of a heterogeneous Indian community. This includes the ‘old’ Singaporean Indian diaspora, which refers to the Indian community that has been in Singapore for several generations, and the ‘new’ expat Indian professionals, who are recent migrants to Singapore. This chapter attempts to outline the trajectories of Indian migration to Singapore and inquire into the consonances and discords among Indians in Singapore with respect to their dissimilar migrant identity formations, ethnocultural practices, transnationalism, and social integration patterns, including the ways in which the newer migrants interact with the settled Indian community and Singaporean society at large.