The purpose of this study was to explore user experiences of three different implementations of digital LSW. Sixteen individuals, including people with dementia (n = 6), family caregivers (n = 6), and care staff (n = 4) working in a dementia care home took part. Participants were interviewed about their experience of learning to use a digital life storybook in one of three contexts: a community group; one-on-one sessions at home; or in a care home. People with dementia and family caregivers took part in weekly workshops for six weeks. Care staff received six weeks of training and were then encouraged to use digital life storybooks with residents. Thematic analyses of each dataset were carried out. Participants enjoyed the intervention, found it useful, and valued the ability to use multimedia stimuli in the digital life storybooks. Limited information and communication technology (ICT) skills was the most frequently cited barrier, and the digital life storybooks were used for some additional unanticipated, but useful purposes. Results of this work provide evidence for the feasibility and positive impact of a supported digital LSW intervention, and the use of digital life storybooks in three contexts. Results also provide useful insight and feedback for the future development and implementation of this approach in research and practice.