We claim that the digital trust research area has tended to privilege the act of trusting while considering distrust a negative outcome. However, from the users perspective distrust might be as valid an option as trust (it may not be a good idea to trade, collaborate or exchange in a particular context). How do we evaluate digital environments that aim to empower trust for the user? This position paper explores some of the complexities. The traditional approach of measuring for an increase in trust is not appropriate. Testing for whether the user has made the ‘right’ trust choice is also unsuitable as trust is personal and idiosyncractic and can only be understood via the perspective of the user. We suggest that the measuring of the reduction of uncertainty before and after a user interacts has potential because it can allow access into whether a user has received the benefit shared by both trust and distrust, a reduction in uncertainty.