There are some era-appropriate limitations, though
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I don’t want to run it on Windows 85/98 but I want that theme for discord
Connecting such an old OS to the internet is a terrible idea.
It was a terrible idea when they were new OSes. I would question if anyone was even trying to attack those anymore, I think they’re still used in Asia and Africa.
Ironically, in some cases it’s more secure because modern exploits flat out don’t work or didn’t exist for it.
For the computer, maybe, but that’s the risks you accept. I’m sure this person understands the risk.