Ageing and migration have become key issues in many European countries, as an unprecedented number of first generation immigrants are currently approaching retirement age. A permanent return to the country of origin seems to be enacted more seldom after retirement than initially envisaged, a phenomenon referred to as “myth of return”. Instead, a third alternative seems to gain interest for ageing migrants, namely commuting between host country and country of origin. The present paper addresses future plans regarding preferred country of residence after retirement and the regulation of well-being of middle-aged and older first generation immigrants. The sample included N = 109 Portuguese first generation immigrants (49.5% female; average age: M = 55.35, SD = 7.42) who had been living in Luxembourg for about M = 30.69 (SD = 8.55) years. Analyses show that only one-fifth of participants plan to return to Portugal, whereas almost one-half prefer to stay in Luxembourg, one-quarter choose to commute, the remainder still being undecided. No differences in life-satisfaction were found, but those who plan to return used fewer self-regulatory strategies compared to those who want to stay or commute; in the STAY group, positive reappraisal strategies were related most strongly to their life-satisfaction, whereas for those who plan to commute both primary and secondary control were beneficial. Interestingly, lowering aspirations was positively related with life-satisfaction for those who plan to return to their country of origin after retirement. Results are discussed taking into consideration aspects of integration and migration experiences over the life-span.