You can configure VirtualBox to work with peripherals. The Whonix documentation is some of the best documentation about anonymity and security on the internet. I think everyone should read it: https://whonix.org/wiki/Documentation It also discusses adding USB devices to Whonix: https://whonix.org/wiki/File_Transfer#Adding_USB_device_to_VirtualBox Apparently there are closed-sourced VirtualBox extensions that will do it. They should allow you to use thumb drives and USB printers. Whonix is based on the same version of Debian as Tails. Not sure if they use the kernel, but hardware support should be roughly the same.