South Africa assumes a significant position in the insurance landscape of Africa. The present research based upon qualitative and quantitative analysis, shows that it shows the characteristics of a Complex Adaptive System. In addition, a statistical analysis of risk measures through Value at risk and Conditional tail expectation is carried out to show how an individual insurance company copes under external complexities. The authors believe that an explanation of the coping strategies, and the subsequent managerial implications would enrich our understanding of complexity in business.