For more than a decade, leading experts in government and industry have warned of an impending Cyber Pearl Harbor, a surprise electronic attack with the potential to neutralize U.S. military power and cause massive disruptions in U.S. and global computer networks. This is a powerful historical analogy – but is it the right one? This paper articulates a framework to better explore and examine the use of historical analogies in their application to conflict in cyberspace. The resulting analysis does not seek to argue the Pearl Harbor analogy is a bad one. Quite to the contrary – our thesis is that while a cyber Pearl Harbor remains a possibility, is should not be treated by decision makers as an inevitability and that there may be equally powerful historical analogies to guide future cyber strategies.