Can't VPN with Windows XP client

Are there any known issues with Windows XP clients and Mac OS X 10.5 VPN? I configured the VPN server in Server Admin and it works fine with a Mac but not with Windows XP computers.

I often can not connect from the outside and get message that the server did not send a response in time. When I do connect, I can't browse my network.

Mac Tower, Mac OS X (10.5.4)

Posted on Aug 29, 2008 11:20 AM

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11 replies

Sep 4, 2008 5:06 PM in response to Peter Scordamaglia

Thanks Peter for you response. I tried your suggestion by enabling 40-bit encryption under PPTP on the server but it made no difference. I am able to connect and I can't ping the server when connected or map a network drive. I get a message that the network path cannot be found.

There does seem to be an encryption or security issue as I am getting about a 75% loss of data during the connection.

Any additional suggestions would be very much appreciated!

Sep 5, 2008 1:02 PM in response to Leif Carlsson

I am using L2TP for Mac and PPTP for Windows. L2TP won't work with Windows. When I try I get an authentication error.

There is no firewall between the server and the internet as I am using a Timewarner cable modem/router which I confirmed with them has no software firewall. Also using an airport extreme as router/gateway which has no firewall settings which is configured to use NAT with the ports designated by Apple.

Any ideas how I can get the GRE protocol to go through?

Sep 5, 2008 5:58 PM in response to wld99

PPTP needs GRE protocol and TCP port 1723 forwarded to the server IP.

Is this the newer type Airport Extreme, the square one with rounded corners?

Latest firmware installed?

Anyhow I think you will have trouble getting PPTP through it.

Some other routers has a VPN passthrough setting that sometimes work for PPTP server on the router LAN.

If you get another router/firewall (like Netgear FVS xxx) get one without a built-in VPN (IPSec) server or you most likely will have problems with L2TP pasthrough.

Sep 5, 2008 10:29 PM in response to Leif Carlsson

In my case, because my server and my clients are behind NAT, I fixed the problem of windows XP connection by adding this in the registry :

1. Click Start, click Run, type regedit, and then click OK.
2. Locate and then click the following registry subkey:
HKEY LOCALMACHINE\SYSTEM\CurrentControlSet\Services\IPsec
3. On the Edit menu, point to New, and then click DWORD Value.
4. In the New Value #1 box, type AssumeUDPEncapsulationContextOnSendRule, and then press ENTER.
5. Right-click AssumeUDPEncapsulationContextOnSendRule, and then click Modify.
6. In the Value Data box, type one of the following values:
• 0 (default)
A value of 0 (zero) configures Windows so that it cannot establish security associations with servers that are located behind network address translators.
• 1
A value of 1 configures Windows so that it can establish security associations with servers that are located behind network address translators.
• 2
A value of 2 configures Windows so that it can establish security associations when both the server and the Windows XP SP2-based client computer are behind network address translators.
7. Click OK, and then quit Registry Editor.
8. Restart the computer.

This info is available on microsoft support site.

Sep 6, 2008 12:54 AM in response to sondens

It's a pity you need to know where you connect from instead of the machine negotiating the connection.

I guess a "2" would be the most useful setting.

And I guess I would use the server (dual interfaces needed) instead of the AirPort, if the public IP is static, as the Internet gw. Or better yet another firewall/router (maybe a Linux based one like Pfsense or Ipcop if money is an issue).

Sep 23, 2008 12:21 AM in response to wld99

You might revisit the TimeWarner modem and firewall. Even though it may allow VPN I have found that many of the home oriented products will only support one tunnel type at a time, ie you can't have an L2TP session and a PTPP session open at the same time, while you can have have multiple sessions of the same type. Most of the Modems from DSL and Cable have a firewall in them but set to UPnP which allows items on the inside to set up and temporarily mod firewall settings but not items from the outside without forwarding in place. Just a thought.

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Can't VPN with Windows XP client

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