Impaired sustainability of livelihoods, threatened survival of wildlife, and altered integrity of environments and ecosystems are the most persistent critical challenges plaguing the Maasai-inhabited savanna rangelands of Kenya. This study engages the Drivers-Pressures-States-Impacts-Responses (DPSIR) model to integratively and simultaneously examine those challenges. Causal social-biophysical components and links driving shifts in the interactions of Maasai’s livelihood strategies/diversifications and terrestrial wild megafaunas via ecological services (ecoservices) are explored; plausible scenarios under changing social-biophysical conditions explicated; and practical interventions illuminated. The study reveals that Maasai’s traditional and emerging livelihoods contextually interact with diverse social-biophysical conditions, particularly those related to land-use/resource-extraction and recurrent/extreme droughts, to occasion diverse and shifting ecoservice-interactions. Sharing of provisioning ecoservices predominate Maasai’s traditional strategies; emergence of heretofore rarely-extracted ecosystem goods become evident as livelihoods increasingly diversify. The study indicates that under recurrent and/or prolonged droughts occasioned by the changing climate, the existing ecoservice-tradeoffs between water needs for arable-farming and livestock, and amongst water-dependent ungulates will, ceteris paribus, intensify. Intensified ecoservice-tradeoffs among wild and domestic faunas under similar ecological-gild and/or trophic-level will plausibly unfold under that scenario. Under the same scenario, lion (Panthera leo) predation on Maasai’s livestock will intensify, and ceteris paribus, increased retaliatory killings of such nuisance terrestrial wild faunas will ensue. Apropos these rangelands, the existence of nuisance lions is revealed as a human generated reality. Collectively, persistent shifts in cross-scale social-biophysical conditions will alter and are altering, in ways yet unknown, the existing ecoservice-tradeoffs/synergies, and therefore the very sustainability of the Maasai’s livelihoods and the survival of terrestrial wild faunas. Therefore, interventions toward ensuring sustainability of ecoservices and of linked livelihoods and terrestrial wild faunas should simultaneously be adaptive to shifts in those interactions and in the changing geography of the various social-biophysical landscapes. The DPSIR model suffices as a practical tool to guide and support such interventions. The need for practical interventions entailing paradigm shift from the existing relevant policies/practices to incorporate the causal-links of the disharmonious human-wildlife interactions, in the context of various dynamic socio-ecological systems, cannot be overemphasized. Collectively, the current study reveals that it is through simultaneous assessment and systematization of the causal and proximate social-biophysical conditions linked to the presently pressing ecoservice-interactions that informed goals can be set, critical indicators defined, and evaluation and prioritization of plausible interventions made.