Post-return migration has been seen as a linchpin that conceptually connects return migration and transnationalism. However, little is known about why return migrants embark on the journey to return to the host country after resettling back in their home country. In recent years, there has been a growing number of Hong Kong Canadians who have returned to Hong Kong, only to resettle back in Canada again. Drawing on the findings of a biographic narrative study of 20 post-returning migrants, this study attempts to explain how the interplay of the changing life-course needs of family and societal contexts influence decision-making processes in post-return migration. This paper reveals how the accumulation and maintenance of transnational resources, such as social networks and cultural experience, intergenerationally provide options for the future migration of migrant families. Based on the findings, we offer a tentative conceptual map for the understanding of the possible pathways of intergenerational transnational migration.