If you're dealing with weird legacy 9x systems in 2026, another headache you've probably run into is getting them to talk to the modern web (since modern TLS and JS completely break old browsers).

I actually built a win9x compatibility mode into BrowserBox specifically for this kind of weirdness. You run the server on a modern system and launch it with bbx win9x-run, and it proxies the modern web to legacy clients. It works surprisingly well with IE5, IE6, and old Netscape on Windows 95/98/NT. Might be a fun addition to your retro utility belt!