For decades, the rhythm of corporate IT has followed a familiar pattern: Microsoft sets an end date for operating system support, and the world scrambles to adapt. This time, with Windows 10's end-of-support looming in October, the stakes feel both higher and—surprisingly for some—much more predictable. For IT administrators who cut their teeth managing migrations from XP, Vista, 7, or 8, the expiration of Windows 10 is not an existential crisis. Rather, it marks another milestone in the...