I’m trying to get an old Windows game running for a friend.

It seems to be a 16bit macromedia app and I kind of got it running in a Win 98 VM using Virtualbox. DOSBox seems to get confused by it being a Windows app.

Thing is, the friend is very much not good with tech and I want to set everything up for him to “just work”. Installing VBox might be a bit too much.

Apparently, you can install Windows inside DOSBox, but is that really stable and usable for layman? Are there any other approaches?

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If it’s a good old game, check if gog.com sells it. That would probably be the easiest way for a non technical user.
Many of their old games run using Dosbox, but without the end user having to set it up, f.e.
https://www.gog.com/en/game/sid_meiers_colonization

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