Wikipedia, an important bibliography and collaborative repository, is dominated by the Northern Hemisphere, in terms of content as well as editor participation. With an under-represented contribution from Global South editors and especially indigenous communities, Wikipedia, aiming at encompassing all human knowledge, falls short of indigenous knowledge representation. A Namibian academia community outreach initiative has targeted rural schools with OtjiHerero speaking teachers in their efforts to promote local content creation, yet with little success. Thus this paper reports on the effectiveness of value sensitive persuasion to encourage Wikipedia contribution of indigenous knowledge. Besides a significant difference in values between the indigenous community and Wikipedia we identify a host of conflicts that might be hampering the adoption of Wikipedia by indigenous communities. Further investigations into the cultural and collaborative gaps are to be done in order to promote an appropriation of Wikipedia by indigenous communities.