REMPAD is a semi-automated cloud-based system used to facilitate digital reminiscence therapy for patients with mild-to-moderate dementia, enacted in a group setting. REMPAD uses profiles for participants and groups to proactively recommend interactive video content from the Internet to match these profiles. In this chapter, we focus on the design of the system and then the system architecture, the system build, data curation, and usage scenarios. We also report a series of steps carried out as part of our user-centered design approach to system development, and a series of analyses on interaction logs which indicate various levels of effectiveness for different configurations of the recommendation algorithm we use. The results indicate high user satisfaction when using the system, and strong tendency towards repeated use in future.