Suggestion: Use a GDB remotely for debugging

[Gravis]

While you may be quite limited by what debuggers will run on Windows 9x, you can bypass this problem by using a GDB stub (like this one) and debugging remotely from the VM host OS. A remote GDB session means you can use any GDB capable debugger including VS Code and probably Ghidra.

I forgot (because I haven't done remote win32 debugging in a long time) but there are prebuilt mingw64 32-bit builds of GDB and the really old mingw builds of GDB(but they need mingw DLLs IIRC) which are suitable for the same purpose.

I hope this suggestion helps.

[friendlyanon]

Building MinGW is trivial with w64devkit (which is also my preferred MinGW distribution) and it produces statically linked binaries. It also includes a patch if you want to target i686. I'm not sure that or the prebuilt you linked are okay for this purpose, since Windows 95 requires at least a 386. Modifying the dockerfile and patch of w64devkit would be a lot easier than fishing for the right prebuilt distribution.

[MattKC]

I had considered doing this but wasn't confident of whether I'd be able to find any compatible GDB build that supported 95 (I'm not even sure if I had managed to get the network working in my VM). But it may be an avenue worth exploring for future work.