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I'm planning to install Trisquel Mini (a derivative of Ubuntu) onto a desktop that previously ran Windows 98, as part of a broader effort to modernize that computer (i.e. allow it to be used with modern applications). The system is from 1999.

As part of the modernization, I'll be replacing the computer's hard drive with an SSD, and use Clonezilla to copy its contents over to the new drive. (This has worked for me in the past; as the contents are copied to nearly-identical sectors, the systems I've used it with haven't noticed any difference.) The former hard drive is much, much smaller than the new SSD I'll be replacing it with, and I'd still like to boot into Windows 98 if needed, so I plan to set it up as a dual-boot machine with Trisquel, by keeping the cloned partition and making a new partition out of the extra space.

The trouble is, if I install Linux onto it, it's likely that my boot sector will be overwritten by the new bootloader. While this ordinarily wouldn't be an issue on a modern system in that GRUB can handle booting into modern (NT-based) Windows versions, I've read some stories that it can cause issues with Windows 98. As such, I'd like to keep the existing bootloader and boot sector as is, with the system booting into Windows 98 the same way as it has been with the original hard drive, to prevent issues with that running.

However, this will leave me with no way to boot into my new Linux installation. After some consideration, I decided that one good way to get around that problem would be to make a floppy disk that I can insert, that the system can boot from and will take care of booting into the Linux install, while taking the disk out will make it boot from the storage drive into Windows 98 as it always has.

How can I do this? How can I install Trisquel onto a separate partition, without it overwriting the boot sector and bootloader of the original Windows 98 installation, while making a separate floppy disk that will allow me to boot into that installation?

I found these instructions on how to make a boot floppy for Linux; can I use some form of those instructions to do it?

If possible, I'd like to solve my issue the way I've come up with here, but other ways to resolve it (e.g. keep a copy of the boot sector before overwriting it as usual) are also fine.

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I don't know where you read that but every installer of a quality distribution will make sure that you can still boot Windows (even Windows 98).

But if you really want to be sure:

  • Boot from a live usb-stick
  • Run sudo dd if=/dev/sda of=/root/backup bs=512 count=1 to copy the master boot record from your disk (sda) to /root/backup.
  • Copy /root/backup somewhere (it's tiny, you can just mail it to yourself)
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  • You'll have to make sure that sda is indeed the hard disk with windows. Check it with fdisk -l
    – Garo
    Jul 31, 2020 at 15:31
  • There's a few things that are worth clarifying here. What @Garo says about installers generally playing nice with Windows is true. The installer for any reputable distribution should let you continue to dual boot. This occurs via "chainloading" the Windows bootloader, as the MBR boot sector is not actually that important to Windows. There's 3 pieces 1. The MBR which loads the bootloader 2. The bootloader, either embedded as part of Windows (sometimes on a separate partition nowadays) or GRUB (will boot Linux OR Windows) 3. The operating system itself
    – Bujiraso
    Jul 31, 2020 at 22:23

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