I have a program called Parsonstech Hebrew Tutor, designed for Windows 98. Evidently it was compiled as a 16-bit program, although it is not DOS, and has a GUI (16-bit Windows program). I have been able to get this to run on 32-bit Windows XP running in a VMWare virtual machine, but that is a lot of overhead for what is otherwise a very simple and could even be portableized program (it is one of those older programs that runs off CD without installation). I don't really want to boot up a whole OS to run this program.

That being said, I have done some research into DOS box, and read a tutorial on installing Windows 3.1 on Dos box, but I do believe this is a full system emulation anyway, and I don't know if the program would run on Windows 3.1 since it is designed for Windows 98.

The most promising thing I have seen is qemu user-mode emulation, which claims it can emulate just the processor and call the program (even 16-bit programs) without running a whole elaborate VM environment. Unless I am misunderstanding it. I tried to call the program as follows:

qemu-system-x86_64 HT.exe

from command line, but it just runs and resets and doesn't open the program. I think I am using it wrong. Can somebody help? Or what are my options? Ideally, I would love to make the entire program and whatever virtualization it needs to run into a portable executable, without installing VMWare player on every computer I use it on. I do not have the source code to recompile it, and the company that made it does not exist anymore, but I don't want to let it die!

  • According to the QEMU docs, user mode emulation is only supported on Linux and BSD. I think you're going to have to boot a VM. You could always try and load Windows 95 or 98 into a VM if that is going to be lighter than XP (don't know that it will be). – heavyd Mar 27 '15 at 17:43
  • There's really no way around it. You're not going to be able to execute 16-bit programs on 64-bit Windows without a virtual machine. – Josh Mar 27 '15 at 18:03
  • Hmm I know I will have to use hardware virtualization of some sort, but the question is if I need to emulate a full system. Windows 95 should be substantially smaller than XP, and I am reading now that it may even run on 3.1, so that is a backup option. If I do end up running it in a Windows 3.1 VM, would you recommend using DOS box or another emulator? Is DOS box faster? Also, am I understanding the qemu command line syntax properly, so that this command would theoretically run the program in user mode in linux: "qemu-system-x86_64 -cpu kvm32 HT.exe" ? Thank you! – Nathanael Mar 27 '15 at 21:00
  • you should throw that away and find a new program. Those programs don't even support Unicode and may cause problems later – phuclv Jul 8 '17 at 17:30

If the app is 16-bit, you could theoretically get away with running the program inside DOSBOX. you would need this: DOSBOX

Once installed, you can run mount C:\foo Z: which will mount the apps folder in DOSBOX. then all you need to do is: Z: and then appname.exe. Just remember to replace C:\foo with the real folder and appname with the real exe name.

  • Thank you. It does have a GUI, though, so I think I may need to install Windows 3.x on DOSbox. But I will try it both ways, just in case. I did read that Windows 3.x has a pretty low processing overhead in DOSbox. – Nathanael Mar 28 '15 at 4:07
  • DOSBOX should be able to launch the app with a GUI, as it does the same for DOS games – td512 Mar 29 '15 at 5:23
  • I just tried it and DOXbox says "this program needs windows." I will experiment with Windows 3.x later today. Thank you! – Nathanael Mar 29 '15 at 15:47

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