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    It is possible if, like you said, your hardware has the ability to boot directly from USB. You will probably need to install GRUB bootloader on the external HDD, or either the HDD was formatted incorrectly. Just note that if you boot from USB where grub is loaded, it may not have the ability for you to select Windows to boot from your internal HDD. Windows also will never have the ability to select to boot either Windows or Debian, unless you install grub on your internal HDD, which I wouldn't recommend unless you are dual booting both from the internal drive. Commented Nov 26, 2015 at 14:14
  • Also note that if you don't have USB set as the first thing to load in your boot order, you will usually need hold/press Esc at boot time every time you want to boot from the USB so that you have the ability to select it (as long as GRUB is installed on the external drive rather than internal). All of this could be wrong, but this is what personal experience tells me. Anyone else, please feel free to correct any of my possible mis-statements. Much of this depends on your specific hardware configuration and setup. Commented Nov 26, 2015 at 14:17
  • Great! In that case, I will actually post it as an answer, and after you accept it as the answer, we can delete our comments. Good to know this fixed your issue. Commented Nov 28, 2015 at 13:27
  • @Chip_North check this unix.stackexchange.com/help/someone-answers Commented Nov 28, 2015 at 14:10