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Why 64 bit OS can't run a 16 bit application?

When trying to play an old game, Skyroads for instance, I get the following error message:

The version of this file is not compatible with the version of Windows you're running. Check your computer's system information to see whether you need a x86 (32-bit) or x64 (64-bit) version of the program, and then contact the software publisher.

If I understand it correctly, Skyroads is a 16-bit program which is not supported in a 64-bit operating system? Is it impossible to get it running on a 64-bit operating system?


Use an emulator like DOSbox for 16-bit DOS games, for more intensive graphics you need to use a VM.

  • 2
    DirectX for 16-bit programs doesn't even exist. – grawity Mar 29 '11 at 17:55
  • 1
    @grawity: Correct, but the underlying GDI display driver was 16 bit back then... :) – Tamara Wijsman Mar 29 '11 at 18:01

The short answer is no, it is not possible to run 16-bit application natively under Windows x64. The long answer is yes. If you're willing to try something like XPMode or other Virtualization software -- you can get it to work.

  • Wrong answer ! Because the short answer is yes. – user2284570 Jul 20 at 18:01
  • Thank you, @user2284570. The linked GitHub solution did not exist when the question was originally answered. Perhaps you would be kind enough to edit the answer with some information on the solution you've mentioned, including details around how well it works in gaming scenarios. – Sean C. Jul 24 at 17:25
  • I tried it on LucasArts Installer, and I didn t noticed a difference than on 32 bits with ntvdm. – user2284570 Jul 25 at 18:14

You can probably install this in xp mode of windows 7. You can download and install xp mode from microsoft. It will function similar to a virtual machine. I think this works in Windows 7 pro and above but there may be some hackery you can perform to get to function in win 7 Home.


Your best bet would be to try running it on a 32 bit os in Virtual Box or Vmware player.

  • Or otvdm which is an unofficial replacement of Ntᴠᴅᴍ on 64 bits Windows. – user2284570 Jul 20 at 18:02

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