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Why 64 bit OS can't run a 16 bit application?
How do I get 16-bit programs to work on a 64-bit Windows?

Here at work my new development machine is Windows 7 64-bit (so I can use extra memory and run VMs). However I have a dilemma: it appears that 16-bit DOS programs do not run under Windows 7 64-bit.

I have an old legacy program written in Clipper that I need to run periodically.

I cannot access the compatibility setting as Windows 7 just greys them out.

  • What sort of output/output does the software do? if it needs something like a serial port or if you need to print, the answer would be very different from if you just need text saved to a file.
    – Journeyman Geek
    Sep 8, 2011 at 7:43
  • Related: gaming.stackexchange.com/questions/1393/…
    – Oak
    Sep 8, 2011 at 8:56
  • I recommend dosbox as well. However back in the day, when the switch to win95 happened at the shop I worked in, our database written in Clipper tested great except for printing. I think it had to with direct access to prn: and lpt: not working with the windows spooler and drivers. It was hard coded.
    – horatio
    Sep 8, 2011 at 14:30

6 Answers 6


For older DOS programs you can try running them in DOSBox Emulator.

  • I downloaded "Dark Forces" from Steam just a week ago and it works on Win7 64-bit using DOSBox. It has an issue when run in fullscreen mode (changing colors, nothing serious) but those disappear if you use windowed mode.
    – Mike
    Sep 8, 2011 at 6:57
  • 1
    @Mike, if it's from Steam, I can imagine it either bundles a DOSBox (clone) or is actually 32 bit code. Many DOS games were 32 bit and ran with a "DOS Extender". Sep 8, 2011 at 7:04
  • 1
    @Jakob It is DOSBox. I only wanted to point out that DOSBox can even handle 'complex 3D applications' from the DOS-era in a 64-bit Win7 environment.
    – Mike
    Sep 8, 2011 at 7:07
  • @Mike, ah, yes, DOSBox is really, really good. :) Sep 8, 2011 at 7:15
  • A generic VM is not as good an option as DOSBox. It is terribly difficult to track down DOS drivers for the emulated hardware in many cases. Much better to use the custom VM which is DOSBox. Sep 8, 2011 at 8:48

You gave your own solution in your question:

so I can ... run VMs

Just run a VM that is capable of running your Clipper application, VMWare with an earlier version of Windows or FreeDOS (or real MSDOS).

Just be aware that you generally need licences to run operating systems in virtual machines (which is why FreeDOS may be a viable option if you can't get a licence for the Microsoft DOS).


If you have Windows 7 Professional, Ultimate or Enterprise then you can use the built-in Windows XP mode.

  • The only app from DOS days that I tried - Turbo C - works in XP mode. Why not try your app in XP mode? its free
    – Akash
    Sep 8, 2011 at 12:28
  • XP mode works but is not suitable for games. It runs a full XP inside an integrated version of VirtualPC. Sep 8, 2011 at 13:52

Might be a bit OT, but since the question is Tagged Windows...

It is also possible to run Win16-Applications through DOSBox since, given installation disks of windows 3.1 or images thereof, it is possible to install and run Windows 3.1x again.

Detailed isntructions can be found here: http://vogons.zetafleet.com/viewtopic.php?t=9405


I would recommend you D-Fend Reloaded.

It includes DOSBox and a graphical user interface which makes it much easier to configure. You can even download D-Fend Reloaded with some freeware games already included and configured.

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The short answer is not without a third party emulation of the 16 bit DOS environment. The long answer is covered in this Wiki Article, http://en.wikipedia.org/wiki/Virtual_DOS_machine , which notes the absence of the NTVDM (NT Virtual DOS Machine) exclusion from the 64 bit environments.

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