Security is an interesting area, one in which we may well be guilty of misunderstanding the very people we are working for whilst trying to protect them. It is often said that people (users) are a weak link in the security chain. This may be true, but there are nuances. In this chapter, the authors discuss some of the work they have done and are doing to help users understand their information and device security and make informed, guided, and responsible decisions. This includes Device Comfort, Annoying Technologies, and Ten Commandments for designers and implementers of security and trust systems. This work is exploratory and unfinished (it should in fact never be finished), and this chapter presents a step along the way to better securit...