This chapter explores dilemmas that immigrants from Italy and Spain may face, when nearing retirement in Switzerland and considering their future country of residence. In particular, the chapter examines these dilemmas from two complementary theoretical perspectives: institutional and transnational. It is argued that both theoretical perspectives, institutional and transnational, are not necessarily contradictory and can be seen as complementary. The relevance of both theoretical perspectives is considered by using data from a survey of the circumstances of Italian and Spanish immigrants nearing retirement in Switzerland, carried out as part of the Swiss National Research Programme on Ageing, together with data from qualitative interviews with these populations.