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I have a decade old laptop that is "working", with Debian 4.x running.
It has working USB, but cannot boot from USB. Its optical drive is powered but doesn't seem to work (I have tried booting several old bootable CDs and DVDs).

To top it off, in my attempts to pull the system up by its bootstraps, I mangled dpkg so apt-get no longer works. I don't have build-essentials installed, either.

It does have network connectivity, so I can fetch stuff off of the internet.

Is there a way to "bootstrap" into a newer OS given the above restrictions? There is no important data on the computer.

I would probably have given up on this computer if it wasn't because it is needed for a charity organization.

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    I don't have a complete answer, but maybe an external usb CD-ROM drive would help? Commented Aug 10, 2015 at 11:07
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    This is probably too complex and specific to get a detailed answer on Unix.SE... If debootstrap still works on your system you could use that to create a new installation of Debian in a folder, then move everything into place. Another solution could be to remove the hard drive and reinstall the operating system using another computer. Commented Aug 10, 2015 at 11:41
  • @JeffSchaller If I had one handy, I would definitely try - but I don't think it'd be able to boot from it as it doesn't boot from USB anyway. Commented Aug 10, 2015 at 12:26
  • @StephenKitt I considered taking out the hard drive as you suggest and that might be the solution. I didn't know that there was in fact a toll called debootstrap, which I will read up on this evening, thanks! Commented Aug 10, 2015 at 12:28

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You can start the Debian Installer from your hard disk. You can do a pure network install (which enables replacing your boot partition during the process) if you boot the netboot kernel and initrd (links for 32-bit PC), or you can do offline installation by booting the hd-media ones and also providing an ISO. This is described in detail in the Installation Guide (relevant chapter linked above).

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  • This looks like exactly what I need! I'll report back after findings. Commented Aug 10, 2015 at 21:49
  • Holy shit this is running through packages now. This is great! Thanks! I wish I could give you a tip, but instead, here's the homepage of the NGO getting this laptop: www.womena.dk Commented Aug 22, 2015 at 21:45

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