Does YubiKey work with an old OS?
If you have an older OS that does not support Universal Plug and Play, the 1st time you plug in a Yubikey you may be led to the driver installation process. In that case follow recommended steps in the pop-up box to install the HID (Human Interface Device) driver that is already inside Windows (or other OS) Updates. If you use a virtual machine like VMWare or a remote desktop, make sure that virtual machine has access to the USB port.