In this chapter we examine two World Heritage Sites (WHS), Great Zimbabwe and Tsodilo, located in Zimbabwe and Botswana respectively, which are both heritage places and areas of on-going settlement. This makes them different from heritage sites in most developed countries where monuments and sites are rarely inhabited or constantly used by resident communities (Keitumetse 2011: 51). Arguably, many researchers and writers in Botswana and Zimbabwe have prioritised and focused their work on the conservation and protection of the tangible aspects of World Heritage Sites, as is required by Article 4 of the Convention for the Protection of the World Cultural and Natural Heritage, 1972. However, this has tended to mean that the safeguarding of the intangible cultural elements, which are mostly upheld by communities linked to these sites, has been overlooked (Coulson, Staurset and Walker 2011; Ndoro 2001; Fontein 2006; Sinamai 2006). The two World Heritage Sites discussed in this chapter, by virtue of their World Heritage status, have attracted a multiple web of stakeholders with overlapping as well as diverging views and interests. This, among other factors discussed in the chapter, contributes to the challenges of safeguarding intangible cultural heritage (ICH) as defined by the Convention for the Safeguarding of the Intangible Cultural Heritage 2003 (ICHC) that are simultaneously associated with places of ‘outstanding universal value’ as defined by the World Heritage Convention.