Setting up a file server is a lot easier IMHO. If you don't feel comfortable reducing protocol security on your daily driver, then you could set up another computer running Samba or an older Windows to put files on. It'd be a lot simpler, IMHO, especially as Windows 3.x and 95 natively support SMB.

Win3.11 with the TCP/IP 32bit package will support WORKGROUPS so you can actually share a folder with win7 and transfer files this way. I don't know about win95 but I assume it will work as well. (on 98SE it's no problem working with workgroups).
I have found though that networking in 3.11 is really slow - even with a 233mmx p1 so I would really recommend using mTCP's FTP server instead: http://www.brutman.com/mTCP/

Hi everyone. I've found a few theads here at vogons that could be helpful.
If nothing works, have a look at Virtual PC 4.x. I think that one also had an x86 version for OS/2 and Win9x (v4.1).
By running a more modern guest inside, It could help to bridge the gap between now and then.

Here are some threads you may wish to browse :

Networking in DOS and Windows 3.1
Win95 <---> Win7 Drive Sharing Issues
Windows 98 PC suddenly stopped appearing in the Network on my main (Windows 7) PC

Windows 3.x security
windows 3.11 share drive problems

This thead was about two physical computers but if interested in VirtualPC then VirtualPC 5.1 with 9x host support.

Can you really run operating systems like Windows 2000 or XP in such an old version of Virtual PC? I would not have thought. I expect you'd at least need atypical amounts of RAM.

I agree that an FTP or SFTP server is probably the way to go.

I use the FTP server on my Router to transfer files between my PCs and Smartphones.

FTP clients can fe found for Win 3.11 , 95/98, XP, 7.... Android......

For example: i download a file on my Smartphone or my Main-PC, then upload it to the FTP and then download it from the FTP with the PC where i need it.

If you wish it is also possible to let the most needed files on the FTP:
windows and game patches, winrar, winzp, Drivers, FTP-Programms etc.

When i setup a new plain PC, i must only be able to get the LAN working, then i can download files from the router with the old Versions of internet explorer that comes with the os.

DosFreak wrote:

This thead was about two physical computers but if interested in VirtualPC then VirtualPC 5.1 was the last version for 9x.

Thanks for the tip! I thought of running VPC on the Win9x machine (with modern guest),
since it also has a folder sharing feature.

Jorpho wrote:

Can you really run operating systems like Windows 2000 or XP in such an old version of Virtual PC?
I would not have thought. I expect you'd at least need atypical amounts of RAM.

Hi, I assume you asked DosFreak - well, my box of Virtual PC v4 for Mac mentions 2K already (even Me! 😉 ).
It may not a pretty experience, but I believe it should run in 32MiB already, 😅

Sammy wrote:

I use the FTP server on my Router to transfer files between my PCs and Smartphones..

Cool idea! Someone here at vogons recently also recommended to use a Raspberry Pi as a Samba server.
Using Samba (*nix) should solve a bunch of compatibility issues between the different generations of
NTLM and other SMB things..

Edit: Silly me! 😊 If it's only about connecting the old machines to one new one,
someone could do the whole VPC thing in reverse also..

I've never had problems using Windows File Sharing and sharing a folder on the OLD PC, then connecting from the new. I've successfully pushed files from Win 7 down to my 98 Install, as well as Windows for Workgroups 3.11. The other way around doesn't work without SAMBA in Linux though.

Sure, shoving stuff manually down the old PC's throat should work anytime.
I assume it's more arduous if someone attempts to access his +20GB software/music/ebook collection he/she has stored on the modern PC or NAS. 😉

zerker wrote:

The other way around doesn't work without SAMBA in Linux though.

I'm no *nix guru, but I believe in Linux or BSD someone can choose between Samba 2/3/4 somehow.
Different SMB versions: https://wiki.samba.org/index.php/Samba3/SMB2

Well, actually what I mean is that SAMBA is robust enough that it will recognize which protocol version you are trying to use and respond accordingly. I didn't do any manual tweaking of my Linux SAMBA exports, and my Retro PC can access my modern shared folders no problem from either ancient version of Windows I have installed.

Least hassle is not to use SMB. 😀

Simple TCP/IP (even mTCP in DOS) and FTP server running on a PC in your network will work fine.

Might be more secure too considering the SMB1 attacks going around.

Found something. 😀

Disabling SMB1 after WannaCry? Make Sure SMB2 is enabled

What You Need to Know About WannaCry Infecting Linux
The legacy code behind WannaCry – the skeleton in the closet

The Deprecation of SMB1 – You should be planning to get rid of this old SMB dialect
What versions of windows are currently affected by the ransomware attack that is in the news?

It seems not to be clear which versions of Windows are affected. 🙁
Scademy says something about ancient code in XP, so perhaps the whole line of NT or OS/2 is affected ?
If so, I wonder if WfW and Win9x are secure then. And how Me fits in the line (W2k network stack).

r.cade wrote:

Simple TCP/IP (even mTCP in DOS) and FTP server running on a PC in your network will work fine.

Server.. pfft.. Null-modem cable and Kermit are way easier. And smoke signals, too. 😉
(But seriously, I'd rather use something like WebDAV. Seems to work in Win98, too. )

Edit: Links fixed.

Setting up Filezilla server in Windows is just few clicks (last version running on Windows XP is 0.9.42)
If you want ftp client for dos, I've used this one built in Necromancer Dos Navigator (requirement is Packet driver for network card running).
On windows Total Commander is the way to go (as ftp client), and there is 16bit Windows 3.x version of Total Commander

Don't get me wrong, FTP is nice and such.. but also, well, crude.
Like anything Unix, basically.

Imagine you want to have Winamp running on your old machine and want to hear some songs
you've stored on the modern day PC or the NAS. With FTP, you'd have to either download each file,
find a plugin, or manage to map the FTP to a drive letter in Windows-Explorer.
https://arstechnica.com/civis/viewtopic.php?f=10&t=656997

Here's an earlier thread about Windows 98 and FTP.
(I wasn't part of it, so it's safe. ;))

Jo22 wrote:

Don't get me wrong, FTP is nice and such.. but also, well, crude. Like anything Unix, basically. […]
Show full quote

Don't get me wrong, FTP is nice and such.. but also, well, crude.
Like anything Unix, basically.

Imagine you want to have Winamp running on your old machine and want to hear some songs
you've stored on the modern day PC or the NAS. With FTP, you'd have to either download each file,
find a plugin, or manage to map the FTP to a drive letter in Windows-Explorer.
https://arstechnica.com/civis/viewtopic.php?f=10&t=656997

Here's an earlier thread about Windows 98 and FTP.
(I wasn't part of it, so it's safe. 😉)

Yes, but the OP said file transfer between machines, not drive mapping and day-to-day usage.

r.cade wrote:

Yes, but the OP said file transfer between machines, not drive mapping and day-to-day usage.

Fair enough. 😊 In that case, the direct cable connection is another alternative. It's part of Windows 9x also.
Personally, I'm more used to other stuff like FileMaven, so I can't really recommend it.
The people at vcfed discussed it, though. The thread can be found here.
Edit: DCC w/ Win7 seems tricky. (A VM could solve that, but we already scrapped that idea..so..)

Jo22 wrote:

Fair enough. :blush: In that case, the direct cable connection is another alternative. It's part of Windows 9x also. Personally […]
Show full quote

r.cade wrote:

Yes, but the OP said file transfer between machines, not drive mapping and day-to-day usage.

Fair enough. 😊 In that case, the direct cable connection is another alternative. It's part of Windows 9x also.
Personally, I'm more used to other stuff like FileMaven, so I can't really recommend it.
The people at vcfed discussed it, though. The thread can be found here.

Laplink also works well, but mainly old-to-old, not necessarily old-to-new...

r.cade wrote:

Laplink also works well, but mainly old-to-old, not necessarily old-to-new...

True, old-to-new doesn't work to well in general also. I'm afraid these kind of problems won't go away in the near future.
As technology evolves, protocols and standards come and go.
I'm running Firefox 28 on an old XP machine and several web pages do cause trouble already.
I don't wanna know how bad this must be for users of much more obsolete technology.