Usually with my Windows XP machines I'm able to have a simple folder sharing system to my Win10 PC via workgroup and LAN. Down to the individual quirks of Windows 98 such as lack of support for NTLMv2, it has trouble ever connecting to said host 10 PC.. I'm able to use the XP system as a bridge between the two of sorts, but as I am often switching that exact PC out, I would like to have it fully independent and connect directly to the 10 PC without resorting to disabling a ton of modern security on the 10 PC. Most notably for this would be having to deal with NTLMv1 or lanman.

Windows 98 IN THEORY should be able to support NTLMv2, and I've seen some people with this same issue in the past be able to make it work, but even with the appropriate fixes (like installing all viable updates, updating IE6, updating whatever Windows install manager thing it was since I already forgot its name) I am still at a loss, with the installer for DSClient crashing the system every time I try to run it. At this point, my options are trying a fresh 98 install, manually adding the DSClient files and updating the registry myself, or using FTP as a means of file transfer. I really like the drag-and-drop nature of the folder sharing though, so I would like to keep it that way if possible.

What are your thoughts? Is Windows 98 just too old to support this kind of file transfer? I mean, obviously it is. But Microsoft themselves were patching it back in the 2000s since businesses were often too resistant to change over their systems, and they still needed to keep them relatively secure until the next upgrade cycle.