Windows 7 did for USB2 devices plugged into a USB1 port: https://www.makeuseof.com/tag/usb-speederror/

If the computer can identify the device’s capabilities (using some kind of bus command, I’m not very familiar with the USB protocol) separately from speed testing the cable+device combination, no reason why it couldn’t work for USB 2/3/4.

Of course, this approach relies on the device accurately reporting its capabilities, which may not be the case for the more cheap-and-cheerful gadgets.

Windows 8 (and perhaps 10, can't remember) alerted me when I used a USB 3 thumbdrive in a USB 2 port

Windows 10 shows a notification whenever my USB-C portable monitor is using USB video (via the monitor's DisplayLink chip) rather than DisplayPort.