Sub-Saharan Africa (SSA) is not monolithic, presenting a challenge for those who want to treat it as a homogenous place for which one approach to Social License to Operate (SLO) suffices. It has various contextual characteristics associated with its different regions, e.g., western, central, southern, and eastern, or calm versus civil unrest. In this chapter, we argue that while SSA is a unique geopolitical entity, it has sufficiently different contextual dimensions that need to be considered when formulating and implementing SLO. We prosecute this argument via a comparative case study analysis approach using projects from Kenya and South Sudan, which are distinctly different countries in their age, regulatory, political stability, institutional, socio-economic, governance, and civil aspects. The findings provide compelling evidence to avoid a one-size-fits-all SLO approach in SSA. Instead, it is recommended to pay careful attention to the contextual (factors) realities in SSA, to be more successful with projects. The insight can guide SSA government policymakers, investors and project operators in the extractive industries and local communities in better instrumentalizing local contextual factors when formulating SLO approaches. This will help them better understand how to deploy and calibrate their expectations around SLO instead of simply relying on off-the-shelf templates that have worked elsewhere in SSA.