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I decided before I commit 100% to a distro that I would dual boot Ubuntu and Xubuntu and see after some time which "feels" better to me. Well, after restarting the computer for the first time I saw this screen:

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I was confused as I saw -two- options for Ubuntu. I know that Xubuntu is a derivative of Ubuntu but why is it showing up as Ubuntu (and not Xubuntu) in GRUB?

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This is normal behavior. os-prober sees the core of the system, not the desktop environment; and this is what it uses to create the boot menu.

The first listing, given as just Ubuntu, is whichever install is controlling grub on /dev/sda.

I'm assuming you installed Ubuntu first, followed by Xubuntu. The menu listings will depend on how you installed the bootloader.

If you installed the bootloader to /dev/sda when installing Xubuntu, then the first Ubuntu listing at the top is Xubuntu and the 2nd Ubntu 14.04 LTS listing is Ubuntu.

If while installing Xubuntu, you installed the bootloader to its partion, say /dev/sda3, then ran update-grub in Ubuntu; then the first listing is Ubuntu and the 2nd listing is Xubuntu.

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