In this paper we outline our approach to discover and understand multi-dimensional correlations among regulatory security certification requirements in the context of a complex software system. A thorough understanding of these correlations is necessary to assure that diverse constraints imposed by numerous certification requirements are adequate for collectively contributing to emergent security properties in a highly interconnected socio-technical environment. We elaborate on methodological support to discover an exhaustive set of applicable certification requirements in a given operational scenario of the target software system. We then describe techniques to systematically understand the multi-dimensional correlations among these requirements with application to security risk assessment. The case study of applying our approach to a regulatory certification process of The United States Department of Defense (DoD) is presented.