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Your system may not be able to see usb devices at boot. Check in bios for a setting that enables USB at boot. If there isn't such a setting, and if your system is fairly old and can't see the device, you'll have to copy the image to a separate partition on the hd.
Quick question, is this a usb 3.0 drive? Try plugging it into a regular usb port on your mobo. Windows most likely does not have drivers for the 3.0 ports. Just a guess. As always correct me if I'm wrong.
Are you running Windows Recovery Environment from Windows install media? Make sure the file is named WindowsImageBackup. Otherwise, Windows will not "see" the image file. Also, have you modified or moved the WindowsImageBackup file at all? It could be just a corrupt image....