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Comment by kmoser | Hacker News Reader

I have a command line Windows binary compiled over 30 years ago (June 1996) that won't run on Windows 10 (64 bit). Windows complains, "ANAGRAMS.EXE is not compatible with the version of Windows you're running. Check your computer's system information and then contact the software publisher."

Is this issue specific to Windows 10, and would it work on Windows 11?

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> is not compatible with the version of Windows you're running. Check your computer's system information and then contact the software publisher

You would receive such response on the every 64-bit Windows starting from Win2003, there is no 16-bit NTVDM in 64-bit systems.

If you need to run it:

a) use 32-bit Windows 10 (Win11 do not have 32-bit variant)

b) use DOSBox

c) ... VirtualBox/PCem/whatever with 'real' DOS.

d) there are some NTVDM ports for 64-bit systems, use at own risk. Ctrl+F in this post.

have you tried various compatibility options? right click -> properties -> compatibility

there's a troubleshooter there, too

I just tried the troubleshooter, and it said it fixed the issue but it actually didn't: when I run the program, Windows pops up a modal (before it just displayed an error on the console) with a title bar that says "Unsupported 16-Bit Application" and a message reading, "The program or feature [...] cannot start or run due to incompatibility with 64-bit versions of Windows. Please contact the software vendor to ask if a 64-bit Windows compatible version is available."

Is it a 16-bit executable?

Yes

64-bit Windows can't use 16-bit executables. 32-bit Windows can.

Almost 30 years ago*

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