A number of technologies have been developed to help users manage their digital legacy, however few user contributions in this space have been solicited from older adults. This is surprising given that older people may have to cope with a digital inheritance but be poorly equipped to do so. The current paper describes three phases of research that explore older adults understanding of and preferences for digital legacy. In phase I, we conducted a large-scale scoping exercise designed to elicit relevant scenarios around digital legacy. In phase II, we presented older adults with a selection of legacy prompts and provocations in order to promote a discussion of digital bequests. In phase III we used life-logging scenarios as prompts in an inter-generational workshop designed to elicit discussion between digital natives and older adults. This work contributes to our understanding of digital legacy from the perspective of older adults and emphasises the importance they place on family, personalisation and control of digital legacy support.