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What is the oldest commercial MS-DOS program that can run on modern versions of Windows (such as Windows 8.1 or Windows 10) without third-party emulators?

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    It's not the oldest, but I still have clients of mine running the MS-DOS version of my accounting software on 32-bit versions of Windows. I even offered to give them my Windows version for free, but as long as they keep paying me support money, I keep the software current (within reason). Specifically, payroll changes for tax revisions. The code itself was ported from Radio Shack Model I in the late 70's, I took over maintenance around 1985, currently MS-BASIC 7.1 – Bill Hileman Jun 17 at 17:49
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    @BillHileman wow, I would think cumulative tax code changes would eat you to death, I.E. the ever increasing complexity would exceed the limits of the legacy platform. – Harper Jun 17 at 21:16
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    @Harper I made the system flexible enough that it's been able to keep up with the changes so far. The last major change I had to made was regarding FICA where a new ceiling was added where a different rate kicked-in, but it's been able to survive with just tax table data entry over all this time otherwise, and yes, payroll taxes are incredibly complex programming-wise. – Bill Hileman Jun 17 at 21:43
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    I'm voting to close this question as off-topic because open-ended "find it for me"-style questions do not work well in the Stack Exchange model. There is no way of confirming the one, true answer, and questions like this inevitably attract a large number of potentially correct answers without specific references or facts to back them up. It is not a practical problem faced in the hobby of retrocomputing or when using vintage computer hardware or software. – Cody Gray Jun 17 at 23:56
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    This is just mindless trivia. I know this site is getting filled with them, but as Cody writes, Stack Exchange is not for such questions. I guess it's because there's no other large forums online for that type of questions, that we are getting all of them here. – pipe Jun 18 at 18:08
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The 32-bit versions of Windows can still run many DOS binaries directly, using NTVDM, and VisiCalc stills works. VisiCalc was available at launch with the IBM PC, so is probably qualifies as the oldest commercial DOS program which can still run on modern versions of Windows without third-party software.

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    Does it in fact run? – Anixx Jun 17 at 13:45
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    I can confirm that it will not run on 64 bit windows 7, but the answer notes 32 bit, and this confirms the exclusion. – fred_dot_u Jun 17 at 14:58
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    Just confirmed it works on 32-bit Windows 7. Takes a little while to start (similar to running debug), which I believe/suspect is because it fires some kind of a 16-bit VM in which to run it. – TripeHound Jun 17 at 15:22
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    @TripeHound It's probably using virtual 8086 mode, not a virtual machine (which wouldn't be capable of that anyway). That also explains why it doesn't work on 64-bit systems, which lack VM86 support. – forest Jun 18 at 2:53
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    @StephenKitt Most virtual machines execute instructions directly on the hardware. If the underlying CPU doesn't support the instructions, a VM can't run it (e.g. you can't have a MIPS program in a VM on an x86 machine). What you would need in that case is an emulator, which is a lot slower. I guess technically the definition of VM can include non-hardware accelerated virtualization (like the Java VM), but usually it's used to mean a hypervisor like VirtualBox or VMWare. – forest Jun 18 at 5:38

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