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I messed up my Ubuntu installation, which is in dual boot with Windows 10, and I'd like to overwrite it with Debian 8. Should I just format the Ubuntu's partition and run the Debian's installer? And what will happen to grub? Will I be able to select the OS at boot?

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Do you have the existing Ubuntu partition backed up? If so, or if you don't need or care about the files on that partition, it would be easiest to simply format it and start over with Debian, as you suggested.

If you need to get files off of it, such as dot files and cfg files, there are free and open source applications that let Windows mount extfs file systems. Then you can back up the files to your Windows partition.

I have a multi-boot system with Windows 10, Debian, Ubuntu, and a couple others for playing around with other OSes and some LFS (Linux From Scratch) builds.. It works great and I use GRUB.

If you want to continue using GRUB, you can re-install it during the Debian installation.

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