drosse1meyer wrote on 2022-07-20, 18:38:
9x Workgroup / file sharing can be notoriously difficult to get working right, even more so if any semi-modern OSes are involved with higher security requirements etc.
Yeah, I've pretty much landed at if it works out of the box then great I guess but I'm not going to jump through hoops trying to make modern Windows or Samba compatible with vintage systems because its not a winnable battle. All those older versions of the SMB protocol have been deprecated for years and support for them is slowly being removed entirely from Samba and Windows for security reasons. Sooner or later no matter how many hoops you jump through it won't be possible for old versions of Windows to talk to newer systems.
So I figure retro computer - retro server. Currently I'm running NetWare which works pretty flawlessly with DOS 3.0+/Windows 3.x/9x/NT/2000/XP as well as OS/2 1.1+ and classic Mac - the only real challenge is getting stuff *on* to the virtualized NetWare server from a modern PC in the first place but FTP works OK for that. Mars NWE is easier as its pretty much like Samba but it implements the NetWare NCP protocol rather than SMB. So you can run both Mars NWE and Samba side-by-side on a Raspberry Pi sharing the same directories via both protocols - SMB for modern machines and NCP for vintage.
Windows NT Server 4.0 in a VM (or perhaps an emulator on a Pi) would work well too. Windows for Workgroups 3.x, 9x, NT, 2000, XP, OS/2 Warp 4, OS/2 Warp 3 Connect Edition should all have no trouble talking to it. The MS client for DOS is absurdly memory hungry to the point of not worth bothering with though - better off using something else like EtherDFS. OS/2 Warp 3 and older aren't possible with out paid-for add on bits from IBM. Classic Mac isn't possible at all AFAIK.