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The world of Information & Communications Technology (ICT) security has been dominated by the Confidentiality Integrity Availability (CIA) paradigm for several decades now and has been very effective in countering relatively simple document based security threats of masquerade, exposure of confidential data, and verification of integrity. Unfortunately real world security problems are not discrete or document based but are complex multi-domain, multi-value ones. In such environments the conventional CIA paradigm is no longer the ideal fit and in particular as we become more reliant on ICT for living support then hard security in the context of CIA needs to be reconsidered. This means taking into account issues that are traditionally “soft” such as Ethics and Dignity and making them “hard” and developing solutions that allow us to treat them. Our starting position is that humans design, operate and are the net beneficiaries of most systems. However humans are fallible and make mistakes. At the same time humans are adaptable and resourceful in both designing systems and correcting them when they go wrong. In contrast machines have in the main been designed to follow rules and are often constrained to produce the same output for the same input over and over again. As we move towards autonomous and intelligent machines the older models of ICT and ICT security based on the CIA paradigm, or deterministic code execution become more and more challenged. Into this mix we then bring a requirement for making ethical decisions.