Within a notoriously restrictive migration regime, the three-tier Swiss pension system introduces differential rights according to nationality, legal status, and place of residence. Some migrants can continue to receive the basic state pension, along with their employer’s pension, while residing abroad, but this is not possible for those in other categories. These rights and restrictions obviously influence the older migrants’ interactions with family members in their home and destination countries, both as recipients and providers of financial support and care on a daily basis. Drawing on life-course analysis, this chapter discusses the manner in which a particular group of older migrants envisages the retirement phase of their lives. The research is based on biographical interviews with thirty male and female Peruvians aged 50+, currently residing in Switzerland. We show that the retirement aspirations of these older migrants are diverse and varied: they may intend to remain in the host country for the rest of their lives, return home on a permanent basis, move to another destination country, or adopt some form of pendulum mobility. We see their plans as the result of complex interactions between host country migration regimes, accumulated pension rights and transnational care configurations, all of which are inherently gendered.