Transnationalism is generally acknowledged as a positive agentic force in the literature describing the transnational experiences of older migrants who stretch their lives between global North and global South. What has been less explored is the extent to which migration policies influence the lived experiences of older migrants travelling from global North to global South, particularly for first-generation migrants who could be viewed as ‘returning’ to their home country. Although the number of older Filipino migrants in Australia is increasing, existing research on older Filipino migrants in Australia has been rather limited. Through the examination of data collected from fieldwork and interviews, this research aims to bridge this gap by examining the lived experiences of older Filipino migrants who stretch their lives across Australia and the Philippines. This research finds that, instead of framing their transnational lives as an agentic response, older Filipino migrants in Australia frame their transnational existence in terms of ‘curtailed dreams’, resulting in an experience that is not widely explored in the existing literature. This research, therefore, calls for a more critical examination of transnational experiences of older migrants who live in a single social field between global North and global South.