Cyber as a domain and battlespace coincides with the defined attributes of a “wicked problem” with complexity and inter-domain interactions to spare. Since its elevation to domain status, cyber has continued to defy many attempts to explain its reach, importance, and fundamental definition. Corresponding to these intricacies, cyber also presents many interlaced attributes with other information related capabilities (IRCs), namely electromagnetic warfare (EW), information operations (IO), and intelligence, surveillance, and reconnaissance (ISR), within an information warfare (IW) construct that serves to add to its multifaceted nature. In this cyber analysis, the concept of hypergaming will be defined and discussed in reference to its potential as a way to examine cyber as a discipline and domain, and to explore how hypergaming can address cyber’s “wicked” nature from the perspectives of decision making, modeling, operational research (OR), IO, and finally IW. Finally, a cyber-centric hypergame model (CHM) will be presented.