In this column, I explore what are known as Wicked Problems. I have recently come to understand that Wicked Problems can be placed in a central position that brings together a number of different ideas which are significant in second order cybernetics. I will start by describing the context in which the Wicked Problem concept was developed. Then I move to explore connections between Wicked Problems and other cybernetic ideas, specifically undecidable questions, trivial and non – trivial machines, and the Black Box. I conclude by discussing the somewhat surprising benefits that we can gain from the concept, and position this with other second – order cybernetic concepts.