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 emulation 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?