This research demonstrates the continual progression of a cybersecurity conundrum that has become an unfortunate but permanent part of the digital environment. Progress is being made, but new fronts open up and new challenges emerge in a seemingly endless cycle. As the need for security rises to a board level concern, cyber leaders are facing more strategic issues to defend against, even while ongoing threats persist. As those security leaders stand to meet the threats, it behooves organizational leaders to provide the support and resources necessary to help enable those they must count on to keep their enterprises safe.