While there is burgeoning scholarship on the transnational lives of Nepali Gurkhas and their families, research on their migration history and lived experiences in Asian contexts is few and far between. Building upon Vron Ware’s concept of Gurkha families as ‘military migrants’ and using an inter-Asia approach as a framework, this article foregrounds the interconnections between military service and migrant pathways during the period of decolonization, particularly in Southeast Asia, and in so doing, offers a gendered perspective on labour migration. Drawing on multi-sited archival and ethnographic research, it seeks to argue that from 1948 to 1971, the Asian region(s) were a dominant feature in the global migration process of Gurkha families who circulated within the arc of a declining British empire. The article further advances that their gendered mobility patterns problematizes the ‘migration–left behind’ nexus as binary opposites as Gurkha wives and children engaged with mobility and mediated their transnational lives in complex ways. It also expands upon the notion of dukha—meaning ‘sadness’ or ‘suffering’ in Nepali—as an analytical theme to yield further insights into their lived experiences and to revisit colonial historiography about Gurkha society.