This field trip proposes a two-day program to understand and evaluate technology adoption of digital wallets among the elderly population in one of the urban slums of Mumbai, through training, probes and shadowing. The aim of the study is to analyse perceived challenges, influences & motivations, barriers to adoption and issues faced during wallet transactions. The findings from this study will be interpreted to formulate design recommendations and guidelines, useful to deploy meaningful propositions suitable for the elderly population, especially to facilitate a smooth transition to the digital vision of India.