What happens when you type "win" at the command prompt?

Did you modify c:\msdos.sys at some point? It should contain BootGUI=1. You can verify this by typing "edit c:\msdos.sys" at the prompt.

If there's something in the autoexec.bat that causes this, you can press F8 at boot to bring up the boot menu, then selecting "Step by Step confirmation", and I believe you can then tell it to skip parsing autoexec.bat.

Thank you for replying.
-typing "win" just evokes the same "you are currently running in MS-DOS mode. Would you like..." prompt I get on boot, when I press "Y" it reboots and same things happen again
-I never tweaked msdos.sys, and yes, it does contain BootGUI=1
-I tried F8 at the start but it just calls up the hardware boot menu (FDD, HDD, etc)

How about typing "exit" at the Dos promt ?

What's the boot process currently look like? Straight into DOS, or starting out with Windows but then rebooting into DOS (like, weird stuff like someone accidentally dragging a "Restart in MS-DOS mode" shortcut into the startup folder)?

What OS even is this? Might that be a WinME "reenable DOS mode" patch gone horribly wrong?

> F8 at the start just calls up the hardware boot menu

That's a BIOS provided one that happens to use the same key. Try dismissing it and immediately continue hammering F8. Or improve your timing and start later, you have like half a second after the BIOS has done its thing and the Windows bootloader starts going.

Typing "exit" doesn't do anything.

The system is Windows 98 SE. It has worked ok for a long time, I used to play games in it, and also used it to boot into MS-DOS mode. The current situation is the remnant of that: I just choose to reboot in MS-DOS in Windows one day, got into DOS, then probably messed something up and now can't go back to Windows.

The boot goes straight to DOS, just showing the autoexec memory/config menu and then the "Do you want to return to normal mode" question.

Ok, I can evoke the F8 menu with step by step and other functions, but not sure what should I do there? If I just say No to every option line, I end up in DOS prompt anyway.

You're supposed to look at the autoexec.bat entries and if there's anything nonstandard, skip it. Then type "win" at the end.

What happens if you hit F8 at boot to bring up the boot menu, then boot into safe mode?

I've never seen that message before "Do you want to return to normal mode". Try googling the phrase and see if it's part of any third party software.

Googling it leads to this: https://web.archive.org/web/20020213151925/ht … os/dosloop.html

So apparently, this happens when you launch a program from Windows using a shortcut that makes the PC restart in DOS mode, for which it modifies the autoexec.bat and config.sys files, and if that program is not exited properly, the config files don't get restored.

Specifically, it's the line "DOS=SINGLE" in the config.sys that causes the behavior of being unable to boot Windows. The fix is to manually revert the DOS mode changes that Windows made to config.sys and autoexec.bat as shown in the link.

asdf53 wrote on 2025-11-17, 18:07:

the line "DOS=SINGLE" in the config.sys that causes the behavior of being unable to boot Windows

Oh wow, that's evil. And not terribly well documented, but I did find this, describing pretty much exactly OP's problem.

The process goes like this:

When you enable MS-DOS mode for a shortcut in Windows and run it, it will backup the current config.sys and autoexec.bat to config.wos and autoexec.wos, and add DOS=SINGLE to the config.sys. When DOS=SINGLE is set and win.com is executed, win.com will restore the config.sys and autoexec.bat files to the original versions and reboot, causing DOS=SINGLE to be gone and Windows to boot.

The only logical explanation I can think of for this "boot loop" to happen is when the backup files are deleted while in MS-DOS mode and can't be restored. Or when the custom autoexec.bat and config.sys contain any commands that would cause win.com to not be able to read and restore the backup files.

The explanation on the site I linked above:

Since the computer has not run the program it is trying to run, the replacement of the autoexec.bat and config.sys will occur again, replacing the backup copies, but this time with the new configuration files.

doesn't make sense to me. The .wos files are only ever written from within Windows before entering DOS mode, and even if you were to reboot the PC before the DOS program has finished running, it would still be copying back the correct files next boot.

@OP do you still have c:\config.wos and c:\autoexec.wos present on your system?

Sorry, I was away from this machine for a while.

An update:
- I don't have the .wos files anymore over there, I think I deleted a lot of backup autoexec/configs in one go at some point
-I tried to REM the DOS=Single . After that the Windows starts to load (shows logo) but gets stuck later and reboots during this process
-I can still get into Win Safe Mode, as well as get into DOS and run DOS stuff ok

I suppose perhaps at this point it'll be just easier to do a reinstall. I still have Win 98 setup files on the HDD. Unless somebody has an idea for a simple fix...