Is it possible to make my USB device work on both Mac and Windows at the same time?

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Regrettably, it is technically not possible to connect a USB device to multiple operating systems (to Mac and Windows) at the same time.

Despite that, Parallels Desktop provides you with the ability to use several types of USB devices in a virtual machine without disconnecting them from Mac. These features have been developed by Parallels especially for synchronizing external volumes, printers, and scanners with Parallels virtual machines.

NOTE: Parallels Tools components must be installed in a virtual machine to receive this functionality.

By default, when you plug a USB device into your Mac with one or more virtual machines running, the New external device detected dialog appears:

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In this dialog, you need to specify where the detected USB device should be connected:

NOTE: If you select to connect the detected USB device to the virtual machine and then reboot this virtual machine, the New external device detected dialog will not appear again after the reboot. The USB device will still be connected to this virtual machine.

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