XP might be OK, but I still wouldn't chance it. Keep windows filesharing within the same generation or at least one off. I can't emphasize this enough: expecting Win98 to work in this way is unreasonable. 98's just so obsolete and so different from newer Windows that there aren't many other good options. If you insist on keeping a physical 98 box, you're going to want a cross-platform filesharing setup like FTP, or SFTP if there's a decent 9x-compatible version of SSH/SFTP. For that matter, I'd turn the Win98 install into a VMware Player virtual machine on the Win8 box and share files between the two with drag-and-drop my 98 (and XP) VM works well on a Win7 host, and I'm sure it'll continue being fine once I upgrade to Win10. At the least, take 98 out of the equation and you'll simplify matters. On top of that, Win98 doesn't support many of the security features that XP and 8 do. Why can I access files one way but not the other? Why is performance poor (sometimes depending on direction)? Why can I see the computer list but not their shares? Why is there a 30 second delay when browsing or using fsmgmt.msc? Why am I getting a cryptic error message instead of a password prompt? (No, Microsoft, I don't want to map it as a drive.) Why isn't the password accepted? Why can't I easily relogin with different credentials or logout? (No, Microsoft, I don't want to use commandline.) Why isn't there a user-based share management interface?īecause they're from different eras, they use very different versions of the SMB protocol. It should be the simplest thing in the world to set up and use, yet it always ends up taking days of troubleshooting and registry editing and web searching and computer restarts to set up.

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