Some people have been maintaining a GCC with 16-bit DOS support for a few years now. It started as near pointer only (so only tiny/small memory models) but now

Some people have been maintaining a GCC with 16-bit DOS support for a few years now. It started as near pointer only (so only tiny/small memory models) but now has far pointers and some memory model support. I haven't really used it in anger. https://gitlab.com/tkchia/build-ia16/-/releases https://gitlab.com/tkchia/build-ia16/-/releases If you want C++ you have to build a cross-compiler from source on a modern platform; they supply DJGPP binaries that'll compile C to 16-bit.