Design Science is the process of solving ‘wicked problems’ through designing, developing, instantiating, and evaluating novel solutions (Hevner, March, Park and Ram, 2004). Wicked problems are described as agent finitude in combination with problem complexity and normative constraint (Farrell and Hooker, 2013). In Information Systems Design Science, determining that problems are ‘wicked’ differentiates Design Science research from Solutions Engineering (Winter, 2008) and is a necessary part of proving the relevance to Information Systems Design Science research (Hevner, 2007; Iivari, 2007). Problem complexity is characterised as many problem components with nested, dependent and co-dependent relationships interacting through multiple feedback and feed-forward loops. Farrell and Hooker (2013) specifically state for wicked problems “it will often be impossible to disentangle the consequences of specific actions from those of other co-occurring interactions”. This paper discusses the application of an Enterprise Information Architecture modelling technique to disentangle the wicked problem complexity for one case. It proposes that such a modelling technique can be applied to other wicked problems and can lay the foundations for proving relevancy to DSR, provide solution pathways for artefact development, and aid to substantiate those elements required to produce Design Theory.