The sharp increase in dementia and age-related memory impairments worldwide has made reminiscence-based interventions attractive. Past research is mixed with little focus on self-functioning. The aims of this study were (i) to develop and assess the implementation of a reminiscence-based intervention, Digital Life Story Books, grounded in evidence-based principles of autobiographical memory, and (ii) to evaluate its effectiveness in improving sense of self in older adults with memory difficulties. A remote reminiscence intervention, using multisensory Digital Life Story Books (DLSB), was developed. Using a short-term experimental, longitudinal design, 25 participants with memory difficulties were assigned to the DLSB condition (16 females; M = 73.96, SD = 8.8) and 23 to a Wait-List Control (16 females; M = 78.57, SD = 9.38). Informal caregivers (N = 34; M = 63.44, SD = 13.8) provided proxy-reports on the effects of the DLSB. The DLSB was successfully developed and positively evaluated by participants. In the DLSB condition, a strengthened sense of self, reflected directly in the memories selected for the DLSB was detected. No overall condition difference was detected pre- to post-therapy. The findings highlight the appeal of reminiscence activities but also the challenge of adequate measurement sensitivity to demonstrate effects.