Solved VPN PPTP client for Windows 3.x or DOS?

February 9, 2014 at 08:04:21
Specs: Windows 7
Hi guys, I am back after many years.

Meanwhile I became a Microsoft certified system administrator (if you can't beat them join them ;-).

I want to know if there is a VPN client for Windows 3.x and/or even one for (MS/DR/OPEN) DOS.

There is one for Windows 95, but I would like to know if there is one that can run with even less requirements.

I hope there is one for (MS) DOS, so I can make a VPN connection from a (very small) virtual machine, so I will post my question in that forum too.

I hope some of the 'old' guys can help me.

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February 9, 2014 at 14:58:01
As for DOS there are packages that are similar to what you are looking for. There is SSHDOS and NetCat. You need packet drivers of course.

Fred's DOS Software

As for Win 3.11 I am not sure...

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February 9, 2014 at 15:24:54
I should mention that I am looking for a PPTP client.

As I wrote I am a MS certified system administrator and I have (several) Microsoft VPN servers running using PPTP and MS-Chap v2 authentication, which are quite easy to setup.

If there is an old implementation of Dial Up Networking (DUN) that can do it (perhaps with TCP/IP 3.11b ?) I would like to know.

For MS-DOS 6.22 one needs to install TCP/IP support first I guess (Lan Manager 2.2c or Microsoft Network Client?).

I have no Windows 3.xx or DOS machine (with TCP/IP updates installed) up and running at the moment, but if I have time I will reinstall these oldies on a virtual machine (although I still have a lot of old hardware lying around, so I am able to run it physically too! ;-)

message edited by Soedesh

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February 10, 2014 at 13:32:21
✔ Best Answer
For MS-DOS 6.22 one needs to install TCP/IP support first I guess (Lan Manager 2.2c or Microsoft Network Client?).

Most DOS internet programs use WATTCP or similar to make an internet connection. Easier than you think to configure for most programs. However, a packet driver for your NIC is required, or else the DOS internet program you use will not work. There is no ubiquitous TCP/IP program that runs in DOS memory all the time - except the packet driver.

Win 3.11 has networking capability built in for DHCP capture or manual setup. It still works today.

If you check out those links I gave you it should get you started and go into more detail. There are no PTP specific programs that I know of. If there are, I'd like to hear about it.

message edited by MisterGopher

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February 10, 2014 at 14:44:58
Long ago I had TCP IP working in both Windows 3.11 and also in Windows 3.1 and DOS 6.22.

I still have the files that I downloaded from MS for it lying around somewhere but they are getting harder to find nowadays.

The 2 websites you gave me are very interesting and the use of WATTCP is something I remember also from the past.

I have to refresh my knowledge and will let you know if I find out more.

I am able to start a VPN connection from the command prompt within Windows XP (with Rasdial.exe) and it must be possible with Windows 95 (and later) too.
Now I am looking for an Operating System with even a smaller footprint than can do this.
I am also thinking of using the WindowsPE (Preinstallation Environment) or BartPE for this if possible.

The sites I used in the past don't seem to be working anymore (I copied and pasted them here from a thread from the year 2005):

There networking with DOS and Windows 3.x was best explained with detailed screenshots and I think I even made a local copy of it (downloaded them to my harddisk) for future reference.
I have to look where they are but can they be found somewhere else on the net now?

I just found an interesting and working (!) website with some good information and screenshots:

I think I will use this as a starting point after I have rebuild a Windows 3.11 machine.
The site is about modem and/or cable connections, but in the screenshots I see you can choose a TCP IP connection with NIC too (at least for Windows 95 and NT).
If MS-Chap v2 is not supported in WFW then I might use an older (more vulnerable) authentication method.
For that I will make an account ( a normal user account if the VPN server is part of a Workgroup or an Active Directory Domain account if it is part of a Domain) with the least privileges as possible (only dial in permission).

Also the MS ftp site does seem to work:

There I found (and downloaded) the file with this description:

March 12 S14540 WFWPTP.EXE WFWG 3.11 PTP Server Update

Which seems to be quite promising.

Also a quote that I found on, which seems to be taken over from

'... Remote Access Service, or RAS, is software that is used for dialing into a RAS server on a Windows NT or LAN Manager Server. A Point-to-Point server for WFW computers was made available via download later. When a client dialed into a Windows NT or LAN Manager RAS server, he or she had full connectivity into the network. If a client dialed into the WFW Point-to-Point RAS server, he or she had connectivity to that computer only....'

Now I would only like to know if the RAS client from WFW supports PPTP connections and if MS-Chap v2 is supported (if not what kind of authentication level is supported?).

According to this article/website RAS with Chap is supported in WFW, DOS and OS/2:

I assume it is Chap version 1, but I would like to know if higher level authentication is supported too.
Also this article is about modem, X.25 and ISDN connections, but I would like to know if connections with a network card are supported too (I guess they must be, at least for Windows 95 and NT4).

message edited by Soedesh

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