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Bug#857646: Choosing where to install Grub by menu selection causes boot failure

Package: installation-reports

Boot method: CD/DVD
Image version: debian-8.7.1-amd64-kde-CD-1.iso, debian-8.7.1-amd64-netinst.iso, debian-8.7.1-amd64-DVD-1.iso
Date: recent
Machine: 2006 desktop with MSI motherboard / 2011 Samsung laptop
Processor: AMD Athlon 64 / AMD A8
Memory: 1 GB / ?
Partitions:  tried various arrangements

Base System Installation Checklist:
[O] = OK, [E] = Error (please elaborate below), [ ] = didn’t try it
Initial boot:                 [o ]
Detect network card:        [o ]
Configure network:        [o ]
Detect CD:                [o ]
Load installer modules:    [o ]
Detect hard drives:        [o ]
Partition hard drives:        [o ]
Install base system:        [o ]
Clock/timezone setup:    [o ]
User/password setup:        [o ]
Install tasks:                [o ]
Install boot loader:        [? ]
Overall install:            [E ]

Comments/Problems: My goal was to install Debian on a portable USB hard drive while leaving my Windows hard drive untouched. Near the end of the install, it asks if it can put Grub on the main hard drive: I said “no”. The next screen presents a menu, an example of which is shown below.

    Enter device manually
     /dev/sda   <description of my Windows drive>
     /dev/sdb   <description of my USB drive>

I selected the third item in the menu and the install completed without apparent errors. In order to use this Debian installation, I must invoke the computer's Boot Menu as it is started. I then select the USB hard drive as the boot device and press ENTER. The screen blanks, the USB hard drive activity light blinks about 3 times, and the computer is found to be unresponsive to everything except the off button. I have tried installing with three different Debian versions on two different computers with two different USB hard drives. I have tried various partitioning arrangements, but the result is always the same, a failure to boot.

However, I have found that I can get a successful installation by doing one thing differently. When I'm asked if Grub can be put on the main hard drive, I still say “no”. On the next screen I choose the menu item “Enter device manually”. On the next screen I type in “/dev/sdb” (from the example shown above). This small change will give me a bootable installation. So my question for you is: why would typing in information give a different result than selecting that same information from a menu? If this is your desired behavior, then I suggest that additional instructions or information would be helpful at this stage.

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