Microsoft sits on the edge of a product launch that is plainly among the most important in the company’s history. It comes at a time when the company’s traditional hardware partners are facing ferocious market pressure from the commoditization of their products, and of course, the juggernaut known as the iPad.

As can be expected, the company’s many cheerleaders and haters are out in full force. Pundits can and will pontificate on Windows 8’s chances. However, what might be more useful is looking at Microsoft’s other make or break moments. The upcoming launch is far from the first time that Redmond has fought with its back against a wall. A backward glance at these moments, and careful evaluation of them, may provide a better, ahem, window into the company’s chances this Winter.

A former presidential cybersecurity advisor stated at a conference on Monday that U.S. computer networks are so vulnerable to attack that they should think twice before going to war with other nations. The shocking claim was made by Richard Clarke...