File share between Windows 10 and Windows 98SE

I’d like to be able to share files between the two.

I’ve followed the instructions here with no luck. I asked the author and he stated he believed a Windows 10 update “broke it”.

This isn’t crucial but it would be a hell of a lot easier to get files to the 98 machine via network that copying them to and from USB drive


If your trying to run a share under a workgroup or similar, this is likely using SMB (I’m rusty on windows tech)

As far as I’m aware 98 doesn’t support anything above SMBv1, and SMBv1 isn’t available on any supported operating system by default because it will leave your system and network vulnerable.

Keep your 98 machine off network. Its highly vulnerable and it could leave patched machines vulnerable as well.


Total noob reply here, nno idea what I am talking about.

Would it be possible to bridge them safely with Linux as the go between that can work with both of them?

This is interesting.
Be sure to block all the spyware from WIN98 LOL

you could use an FTP server. or make a small apache server with a PHP upload

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Anything Windows Vista and earlier should be dark and be on a heavily restricted VLAN with no outside access.

We have some windows server 2000 machines that run dark because it is not safe to have then safe on the network with other more modern clients due to their security risk.

If you must share files between them then you should keep using a flash drive/external hard drive. Do not, and I repeat, DO NOT have them on the same network unless on separate VLAN’s.

Nope. The protocols they support are too old and full of holes to be used in conjunction with newer OS’s.


My company just got hit with WannaCry a few months ago and if it wasn’t for VLAN’s we would’ve been fucked . We have 600 machines on our network.

Its no joke; do not network anything less than Windows 7 together.


Here is an example of why they are not safe (even when your other computers are patched.)

The headlines were from phase one of the experiment were:

  • The customer ran it on one machine in their engineering network with no privileges.
  • It found three machines unpatched.
  • It exploited those three machines to obtain kernel level access.
  • It infected those three machines.
  • Within ten minutes it had gone through the entire engineering network using recovered/stolen credentials.
  • It then took the domain about two minutes later.
  • 107 hosts were owned in roughly 45 minutes before the client initiated the kill and remove switch.

As kenkoda said.
FTP service is the safest easiest and most compatible method you could use.

If this is just a home network with a windows 98 retro gaming PC or something then it should be fine.

For all other scenarios that Win 98 machine should be isolated/firewalled to it’s own without internet access.


i think it would be the easiest way to compartmentalize an instance of 98SE. Even if the FTP is running on the win10.

i would feel better having a linux running the FTP betwen the two, like a PI or otherwise something small if they dont have a linux in house already

if VMs are an option you could make a vlan for the 98 that has a gateway of an VM thus keeping it unable to have any unwanted network access regardless of direction

Wow. Got to admit, 98% of that went over my head.

My take away though was:

  1. Its not going to be easy

  2. I would probably need some third device as a go between

  3. Its dangerous. Just don’t do it.

Unless I missed something I think I will just stick with USB for short 1 time jumps and DVD for multifile repeading needs.

Thank you all for your time. I do appreciate it.

I would just get some FireWire cards and have a hard drive in between them. That doesn’t seem that hard TBH.

older windows clients and new windows file sharing has become a constant pain .

the over hyping of security has made it near impossible to get a working solution any more because of the DREAD that running an old windows client causes some people.

most likely the simplest method will be to use a virtual machine that allows for access from windows 98 and also windows 10 .

with the last smb vulnerability however that may be difficult to accomplish but still doable with some trial and error.

worse comes to worse a ftp server on the win 98 machine and maybe something akin to rsync on the win 10 machine will get you close to what you want.

it may also be quite possible to virtualize that win98 machine and host it on you win10 machine.