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The meta question Is emulation on topic? has multiple highly upvoted answers, all of which agree that emulation of retro systems is generally on-topic, to one extent or another. The top-voted answer (with 33 upvotes and zero downvotes as of my writing this, meaning everyone who read it apparently agrees) implies that troubleshooting retro software under an emulator is on-topic, mentioning this as an example:

For example, "I can't get SimCity to play sound in DosBox" is on-topic because it has a corresponding non-emulated question: "I can't get SimCity to play sound on my IBM-compatible".

It’s not hard to stretch this to cover Windows 95.

The wiki for the tag lists as an example question:

Which Commodore 64 emulator offers better compatibility for ⟨game⟩?

which again, suggests that questions about compatibility of emulators with retro software is within scope.

Despite this, How can I get Windows 95 to run in DOSBox? was closed as off-topic. The only justification given for this is ‘DOSBox is modern software’, in spite of DOSBox specifically, and compatibility with emulators more generally, being explicitly mentioned in examples of on-topic questions elsewhere. What gives?

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I don't think the question is off topic.

The problem seemed to be that DosBox isn't designed to run Windows, which is a problem with DosBox, and therefore with the modern software environment. However, the user asking the question can't be expected to know what the answer is.

In general questions about running Windows 95 on modern hardware should be on topic. If the question had read 'How can I emulate Windows 95?' it would have been ok.

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    ‘Your approach is a dead end’ is an answer to the question, not a circumstance that puts it out of scope. It is nowhere said that every on-topic question must have a ‘yes’ answer.
    – user3840170
    Commented Aug 2, 2021 at 9:54
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    I have clarified my answer to make it clearer that I agree.
    – Mark Williams
    Commented Aug 2, 2021 at 14:11
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    And the question is open again.
    – Mark Williams
    Commented Aug 3, 2021 at 18:00
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I think it's clearly off-topic, even though emulation is generally on topic. This is a case that we know the configuration is unsupported by the emulator's developers, and trying to get it to work is better directed at looking at a different emulator. Entire forks of this particular emulator exist to run out-of-original-scope applications.

Any question “How do I run ____ under DOSBox?”, where ____ ≠ a DOS game should be off-topic.

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  • This being a retrocomputing site, we kind of regularly deal with situations where the manufacturer does not support a given configuration. The old-hardware-adaptation tag is probably the best source of examples. I don’t think emulators are exceptional in this regard. Would ‘How do I run Windows 95 under FreeDOS/DR DOS/IBM PC DOS 7.x?’ be off-topic as well, because the vendors of those do not support running Windows 95? (Or maybe because FreeDOS is an ‘emulator’ of MS-DOS that just happens to run guest code natively on bare metal?) FreeDOS is just as actively maintained as DOSBox.
    – user3840170
    Commented Aug 5, 2021 at 13:19
  • (Which is to say, not especially, since DOSBox hasn’t had a release in two years, and gets just a couple of commits per month in its SVN repository, with FreeDOS having roughly similar levels of development activity, so I’d argue both count as ‘barely maintained’.) And if you worry about having to answer repeatedly asked variants of ‘How do I run [non-game software] in DOSBox’ with ‘you don’t’, this is usually handled by a canonical duplicate question.
    – user3840170
    Commented Aug 5, 2021 at 13:21
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    You're going a bit reductio ad absurdum there. There's a big difference between running a configuration the supplier could not have conceived of (like Win 95 on FreeDOS) and running a configuration that the developers have repeatedly said "we don't support this, don't ask". The very definition of this site is, if it's still in warranty, it shouldn't be here!
    – scruss
    Commented Aug 6, 2021 at 22:32
  • FreeDOS was founded because of Windows 95, so this configuration could definitely have been conceived of. (I’m not sure what the developers’ stance on it is; I presume it is just not a priority, but efforts to support it might very well be not outright rejected.) And as before, it’s just as much ‘under warranty’ as DOSBox. What’s wrong with an ad absurdum? It’s a valid argument. I want to arrive at a principle, not a gerrymandered hodgepodge of ad-hoc exclusions.
    – user3840170
    Commented Aug 7, 2021 at 7:54
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    The FreeDOS project started in 1994, more than a year before Windows 95 was released. Running Windows on FreeDOS is still not recommended. We are very much working in an ad-hoc space, so we're either gonna have a complete principle, or a consistent one. Not both.
    – scruss
    Commented Aug 7, 2021 at 17:30
  • Give me consistency then. I can live with incompleteness.
    – user3840170
    Commented Aug 9, 2021 at 18:45
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The main point for this question being off topic is not that it is a question about an emulator and emulator specific topics, but that

  1. it is about usage of an actual software still in development, with an active development and maintenance site/community

which is the most important point for closure. Lesser, but as well important,

  1. it does not ask for workings of the emulation or problems that would occur with the emulated classic hardware, but issues that only occure with that emulation - after all, Win did install million times well on real PC.
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  • This completely ignores the examples, some of which explicitly mention DOSBox.
    – user3840170
    Commented Aug 9, 2021 at 14:59

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