This chapter presents our latest interventions within the ongoing digitization of cultural heritage of the ovaHerero and ovaHimba indigenous communities in pastoral Namibia. It describes the communicative and technical processes undertaken in a number of sessions at four different sites over a one and a half year period. These sessions were part of the co-design, co-development, and future implementation of an Indigenous Knowledge (IK) Crowdsourcing Management System that aims to provide and to empower elders from rural ovaHerero and ovaHimba communities with extended tools to gather, store, classify and curate their traditional knowledge. Applying co-design as the process aims to ensure users are involved in the design process ensuring their needs and concerns are elicited and suitably addressed. As such this chapter introduces first the background, rationale and scaffolding of the project. Then it pronounces the aims regarding the technologies intended for deployment, their current co-design and co-development phases, and the methods positioned in each session discussed in order to progress in the design endeavours of our multidisciplinary team of researchers and local communities in four villages, namely Erindi-Roukambe and Okomakuara for ovaHerero, and Ohandungu and Otjisa for the ovaHimba ethnic group. Further, it details the initial take-on, engagement, and participation of partakers in Usability and User Experience co-design sessions. The chapter closes stressing the challenges revealed and the future projections thus-far unfilled.