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Accelerating globalisation and contemporary transnational migration impact the way that citizenship is given meaning and practised by both states and citizens. Based on a study of the Singaporean state and highly skilled Singaporeans in London, this thesis advances an argument that transnational migration opens up new avenues to think through citizenship as a distinct spatial and socio-political formation. My thesis investigates, first, the manner in which Singaporean transnational migration informs existing understandings of highly skilled migration and second, the dynamics of the relationship between transnational migration and citizenship. I utilise discourse analysis, ethnography and in-depth interviews with Singaporean policymakers, London- based Singaporean community associations and individual Singaporean transmigrants to carry out my study. This thesis develops the scholarship on middling transnationalism by drawing attention to the fluidity of migration strategies and the institutional factors that motivate 'highly skilled' Singaporean migration to London. My research findings also contribute to geographical perspectives on transnational migration and citizenship in several ways. I introduce the concept of 'emotional citizenship' through narratives of place-based belonging. However, I also argue that identity politics disrupt notions of a coherent Singaporean identity and transnational community. I further propose that mobility creates spaces of contradiction in the way that citizenly 'rights and responsibilities' are relationally constructed by the Singaporean state and its citizens. Finally, I focus on Singaporean transnational families to highlight the spatial significance of the 'Asian' extended family in relation to citizenship issues. This analysis foregrounds the mutually constituting relationship between the emotional, political and social-cultural aspects of citizenship. Whilst this thesis presents empirical reflections and policy implications that are specific to the Singaporean case study, my findings also contribute to broader theoretical formulations of transnational migration and citizenship (trans)formations.