Yeah, windows is a hydra of weirdness, where some things fully support longpaths, but random things will come up that don’t, or fail to properly check and handle things, because no one ever got around to fixing it.

But even the linux kernel will quickly start having problems if one starts having long filenames with multi-bit unicode characters, that 255 bit size max can go fast. Many filesystems for linux actually support larger filenames than what the kernel does.

This is not just a Windows thing. Plenty of Unix software struggles with long paths as well.