The objective of this paper is to serve as a decision aid for energy security policies and programmes in the context of a low carbon energy transition in South Africa. A concept-to-design prototyping matrix for energy security planning inclusive of energy services is presented. It is recommended that energy security design and planning frameworks should be self-defined and government accepted at the country level to be effective for sustainable energy development. The tension between energy security and energy transition is identified as a systemic risk and the concept of a meta-indicator is introduced to measure this transition gap which is modelled along an adaptive frontier. Complexity is explored as one of the three hallmarks of risk, as well as in its contribution to measurement challenges. A multi-scale, multi-speed heuristic model of a socio-energy system transition is illustrated and indicative South African energy supply and demand baselines and risk indicators are measured. The ratio of useful exergy output to final energy input (25%) is advanced as the efficiency indicator “closest” and “earliest” to energy services, and a transdisciplinary monitoring and evaluation framework centred on jumping indicators is proposed for strategic monitoring and evaluative learning. Adaptive programmes are recommended because they are antifragile, and the concept of a resilience boundary is introduced for further development. A specific planning and monitoring tool is proffered together with other methodological options for future needs based applications.