A recurring principle in consideration of the future of systems engineering is continual dynamic adaptation. Context drives change whether it be from potential loss (threats, vulnerabilities) or from potential gain (opportunity-driven). Contextual-awareness has great influence over the future of systems engineering and of systems security. Those contextual environments contain fitness functions that will naturally select compatible approaches and filter out the incompatible, with prejudice. We don't have to guess at what those environmental shaping forces will look like. William Gibson famously tells us why: 'The future is already here, it's just not evenly distributed;' and, sometimes difficult to discern. This paper provides archetypes that 1) characterize general systems engineering for products, processes, and operations; 2) characterize the integration of security to systems engineering; and, 3) characterize contextually aware agile-security. This paper is more of a problem statement than a solution. Solution objectives and tactics for guiding the path forward have a broader range of options for subsequent treatment elsewhere. Our purpose here is to offer a short list of necessary considerations for effective contextually aware adaptive system security in the future of systems engineering.