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The Maasai pastoralists inhabiting Kajiado County have been known for their rich cultural values which have sustained their livelihoods. However, these cultural practices are evolving under the swift development context with the private holding of land becoming more prevalent. Before these disturbances, customary land was available for the Maasai pastoralists to carry out traditional production systems. The disturbance in their social-cultural ways following land fragmentation has rendered their traditional governance system untenable. Moreover, the Maasai pastoralists have been dispossessed from their customary land and social institutions which have shaped their customs. Thus, concerns have been raised over the sustenance of pastoralism considering that the required resources are either unavailable or not enough. To address this gap, there was the need to understand cultural adjustments and their impacts on the Maasai pastoralists’ societal needs. The study employed a cross-sectional design which consisted of 195 Household survey questionnaires, 8 Focus Group Discussions and 18 Key Informant Interviews. The qualitative and quantitative data from the study were summarized and thematic perceptions generated. The results of this study revealed the uniqueness of the Maasai pastoralists’ traditional social structures. Also highlighted by the study was the erosion of the traditional social relations exposing the Maasai pastoralists to increasing vulnerability. These findings support the need for external support to supplement the traditional coping strategies to balance the ecological, social and economic systems of the Maasai pastoralists.