I would also like to know this, and NT 4 as well.

If you're looking to transfer files from a newer version of Windows, like 7 or 10, to and older version like 2000, 98, 95, 3.1 / WFW, it would probably be easiest to use shared folders. I usually set up my older rigs with shared folders, and map their drives under Windows 7. The downside is that you can't access shared folders under 7 or 10.

For all my Win9x setups I use a network folder hosted by a Dell Latitude hooked up to the ethernet card, which also serves as a WiFi-to-ethernet bridge so I can go online. It's not terribly hard to set up, I just enabled Internet Connection Sharing and file sharing in Windows XP and it even works with my 486 via mTCP.

You can use tools to mount FTP and WebDAV storage volumes in Win98.

There's a built-in a FTP server in Windows 10. It needs a lot of configuration though, so if you have another somewhat modern computer lying around — just use Ubuntu Server & vsftpd. It's a lot easier to get running, frankly.

Or FreeNAS.

ElementalChaos wrote:

For all my Win9x setups I use a network folder hosted by a Dell Latitude hooked up to the ethernet card, which also serves as a WiFi-to-ethernet bridge so I can go online. It's not terribly hard to set up, I just enabled Internet Connection Sharing and file sharing in Windows XP and it even works with my 486 via mTCP.

I did this with a raspberry pi

I'm not using any kind of ftp software, I'm using samba. I can even access the share from MS-DOS and windows 3.x

I use also Samba in a small Linux VM. I can map in any host folder into the VM and share it through Samba. Works as Deksor said even when accessed from MS Lanmanager in MS-DOS.

Samba is the right answer, it's been in Windows for ages. Some configuration will be needed in order to allow older versions of windows to connect to newer versions of Samba, as they have higher security requirements.

I also use DVD+RWs a LOT. They are my main method of sneakernet data transfer. Flash drives are a lot slower, and are hard to set up on DOS.

I have my own personal website so I just use WS_FTP and transfer stuff that way between machines. Works fine for virtually any OS as long as you got an ethernet adapter in your old machines.

What's wrong with a modern ftp server on the modern machine (launched at will, not always running) like Filezilla FTP Server which needs 2' to configure and an older version of Filezilla FTP client for the Win98 PC? Filezilla is of course only one easy choice, many more programs are available. I'm just finding it an overkill to go to things like samba for a simple file transfer, unless you have some file server already running for other reasons.
An additional benefit for using an FTP server on the modern machine is that there are FTP clients virtually for everything, so even a DOS pc can run a client and get files.

Ampera wrote:

Samba is the right answer, it's been in Windows for ages. Some configuration will be needed in order to allow older versions of windows to connect to newer versions of Samba, as they have higher security requirements.

I also use DVD+RWs a LOT. They are my main method of sneakernet data transfer. Flash drives are a lot slower, and are hard to set up on DOS.

Also mounting my file server's SMB shares on my W98SE rigs. If I remember it right, you can configure W98 to access the shares with the default Samba authorization config if you rather like that, but I prefer doing it the way you describe too. It's not like it's a security risk on your home LAN behind a NAT router anyways. Just add:

1lanman auth = yes

...to the [global] section of smb.conf, and restart Samba. Then you should be good to go.

The SMB/CIFS protocol has a lot of overhead and is quite slow especially with older Windows OS that don't support more modern SMB 3.x. XP and before only support SMB 1.x which was extremely slow. If you prefer a bit of convenience over speed then go for it. I certainly wouldn't call it "the right answer" by any means, but it's a valid option in some situations. Using SAMBA is even more overhead than MS's native, though maybe it supports later SMB protocol versions (it supports SMB 3.1 on Linux with current versions, but I'm not sure about other platforms; I actually use Linux as my primary OS so that's what I'm familiar with in this case).

FTP is another option and is faster and lighter but a little bit less convenient. You should be able to use the free Filezilla and Filezilla server, or perhaps some of the old good ones like FlashFXP (I'm not sure if that's still around these days). I've also used CoreFTP as a client and that was pretty decent also.

98SE also supports USB2 if you prefer. I'm not specifically recommending USB flash drives, but it's an option in some cases as well.

Also see here for an HTTP based solution Re: FTP for drivers?

If you're wanting to transfer only a few files, another simple (but not necessarily easiest or fastest) method could be using the file transfer abilities built into VNC clients and servers. You would lose some transfer speed from the overhead caused by the screen sharing, and if the server is running on the older computer the performance penalty caused by the CPU load could slow things down even more, but it's otherwise one possibility to look into that's fairly easy to implement.