Which Windows version first supported USB natively?

The first Windows version to support USB natively was Windows 98. Microsoft designed it to make USB peripherals easier to install through built-in drivers and plug-and-play hardware detection, reducing the need to configure legacy serial or parallel ports manually.

Released to manufacturing on May 15, 1998, and generally available on June 25, Windows 98 arrived as USB hardware was becoming common on desktop PCs. Its native USB support helped devices such as keyboards, mice, printers, scanners, and other peripherals identify themselves when connected. Microsoft described Windows 98 as the first major Windows upgrade to take full advantage of USB technology.

A common mix-up is confusing general USB support with support for every type of USB device. Early Windows 98 editions did not include complete built-in support for modern USB mass-storage devices such as flash drives; those often required separate drivers. Windows 98 Second Edition improved compatibility, but Windows 98 remains the standard answer to this historical question.