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I'm restoring an old Thinkpad E310ed from c. 1997 and running into an issue I can't seem to find a workable solution to: installing Windows 98SE to a new "hard drive." The original HDD seems dead (BIOS detects but drivehead/platters sound awful to the point it's ear-grating) and I've purchased both a 2.5" IDE-CF and IDE-SD adapter. The CD drive in the laptop seems dead as well; it spins up and makes a liquidy sound for about a minute before going idle. Booting from the CD drive has been unsuccessful with every ISO I've tried. There is no floppy drive to make use of. So what I'm left with is the need to install Win 98SE to either a CF or an SD card--through the adapters--and to use that as the disk drive as well. Here's a mostly-complete list of everything I've tried that hasn't worked:

  • Booting MS-DOS (installed via Rufus) from the CF drive
  • Booting MS-DOS (installed via Rufus) from the SD drive
  • Installing Windows 98SE to a similarly-spec'd virtualbox machine, converting to VHD, then using hddguru's raw disk tools to "flash" the virtual Win98SE install to the SD card
  • Same as above except I interrupted the Win98SE install right after the copying files to drive step before actual set up begins
  • Any and all CD-ROMs will not boot
  • Partitioning the SD drive and flashing the Win 98SE ISO to it, then attempting to boot from HDD
  • Setting HDD to "none" in the BIOS (this was a fix that worked for some CF card users when it came to older BIOS's not recognizing drive dimensions, like heads and cylinders)

All of the above resulted in the same error: DISK BOOT FAILURE, INSERT SYSTEM DISK AND PRESS ENTER.

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Responses to Comments (as of 10/31):

  • I do not have an extra IDE hard disk, unfortunately. I also do not have any other boot options besides those listed above. There is, annoyingly, no non-proprietary floppy connector (and I cannot find compatible pin-outs for the proprietary external floppy connector). There is also no internal FDD header.
  • I had this thought about CD-R compatibility but, unfortunately, do not have access to a pressed OEM CD (the only bootable Win 98SE discs).
  • Windows 98SE OEMs were bootable. See https://winworldpc.com/product/windows-98/98-second-edition ("Important: Only the OEM Full version is bootable. All others require an appropriate Windows 98 Boot Floppy.").
  • The 310ed's BIOS actually explicitly supports boot from CD-ROM which was a surprise! Just too bad the drive is either busted and/or I don't have a compatible CD.
  • The error message is definitely from the ROM BIOS as it is present regardless of attached drive.
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    If booting MS-DOS from the CF/SD drive didn't work, I'd suspect either incompatibility, or some hardware issue. Can you test with an extra real IDE harddisk? Do you have any other options to boot from besides HD and CD? Does it already have USB? Does it have a floppy connector so you could attach an external floppy drive?
    – dirkt
    Commented Oct 31, 2023 at 5:49
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    installing to a virtual machine is nearly impossible, you need to get the chs translation to match, and it never does. 1997 is far too early for USB boot, 1997 era cd drives often (not always) can't read modern CDR, or any after the dye changed to allow 16x writing. Try a pressed retail win98 CD, or change the cd drive,
    – camelccc
    Commented Oct 31, 2023 at 10:00
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    Problem is, it doesn’t boot at all. The message “DISK BOOT FAILURE, INSERT SYSTEM DISK AND PRESS ENTER” usually comes from the ROM BIOS, which means that it apparently cannot even load a valid MBR from the drive. Commented Oct 31, 2023 at 14:45
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    You can try looking at the boot sector of your CF/SD card in another computer: check if it has the 55AA signature, partition table and boot code. Perhaps it’s not the hard drive that’s broken, but the IDE controller. If you can connect the original hard drive to a USB/IDE adapter, you may also see if that works any better than connecting it to the original laptop. Commented Oct 31, 2023 at 15:03
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    if you actually want to install to a VM, you are going to have to use the laptop bois to determine the CHS the laptop is expecting for that card controller combo (note down the detected CHS settings), manipulate the image so the chs matches, like the guy in this thread did, forums.virtualbox.org/viewtopic.php?t=63454 and then install to the vm.
    – camelccc
    Commented Nov 1, 2023 at 11:21

1 Answer 1

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Put the hard drive (or flash card) in another computer. With all storage devices being broken it is the only way. Obtain a Windows 98SE start up disk or earlier DOS boot disk, or boot from your CD. Run fdisk and then format the drive. run sys c: to make the drive bootable assuming it is drive c.

What size is the SD card in the SD drive? The original SD card readers before SDHC cannot work with an SD card over 2GB. It is a hardware limit. Does the BIOS recognize the presence of the drive? It should detect it and show you the size, otherwise it is not working.

The "other computer" can be a VM. Make sure you know what hard drive CHS values the virtual BIOS in the VM is presenting to DOS. Some older BIOS have bugs with larger hard drives.

If you get past that part successfully most of the work is done since that is the hard part. The CHS values of both computers must match or else the CHS in the partition table and the CHS stored at the beginning of the bootable partition won't match the BIOS and it won't boot. You can probably turn translation on (8.4GB limit) or off (504 or 528MB limit) on the Thinkpad. The same on the other computer. They need to match. If the Thinkpad doesn't support extended INT 13h then you'll have to have translation enabled or you'll have the 528MB limit, and Windows 98 won't fit. Same applies if you use an old version of DOS that doesn't support extended INT 13h. You have to obtain the boot floppy or boot off the CD. I assume the Windows 98 CD boots in to DOS. I haven't used one before.

Once you have bootable DOS working, it's a simple matter of copying the win98 directory on to the drive before moving it over to the Thinkpad and running win98\setup.exe from inside DOS. Make sure the drivers to get networking going are copied as well, because a network share, direct serial cable connection, or infrared (if equipped) are going to be the only ways to copy files over.

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