This paper uses Charles Tilly’s processes and mechanisms of democratization to explore best practices and barriers to democratizing the relationship between the Government of the Republic of Namibia (GRN), and San citizens, who are a minority Indigenous Peoples. The research incorporates an intensive literature review as well as participant responses from field research in Namibia during February 2018. While San-GRN relations dramatically improved after independence, the ongoing democratization eventually hit a glass ceiling for San Namibians. A deeper investigation reveals that San-GRN democratic communication platforms are often co-opted, the San hold unstable access to NGO political resources, and that arbitrary decisions continue to be made on behalf of San citizens by public officials. The research finds that unsupportive institutions, as well as maintained and reinforced stereotypes of the San as ‘incapable’ in public politics have become core barriers to democratizing San-GRN relations. Importantly, despite the GRN approach of denying ethnic power relations in contemporary politics, the San continue to be excluded from the full benefits of democracy due to their ongoing unequal relations as a collective identity. By engaging in a qualitative process-tracing assessment to explore how the democratic relationship between the GRN and the San has changed since independence, this study provides evidence-based best practices and barriers which can be used by the San, the GRN, and their supporters in their efforts to improve their democratic well-being.