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This article deals with transactions in which older people pledge their assets in exchange for the provision of life annuity care. Although little considered in the life annuity literature, which tends to focus on the financial dimension of property sales, these transactions are undertaken in a variety of contexts. In Cuba, “legacy for life care” arrangements, involving both related and unrelated individuals, are common. Based on surveys conducted since 2010, the paper shows that these transactions respond to the care poverty of many older people, while few institutional or market alternatives exist. They are favoured by inheritance laws, intergenerational solidarity practices and the occupant protection laws enacted by the revolutionary regime. Recent reforms are substantially changing these parameters: the property market has been restored, migrant children can now claim their inheritance rights and paid care provision is increasing. However, the assets of older people still play a central role in end-of-life security, which does not obviate the need for public policies that share more widely the responsibilities for the care of frail individuals by the public and private spheres.