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Strange Windows 10 client settings behavior, using L2TP and http proxy in standard mode

ErikFranzén

I have a peculiar Windows 10 behavior which somebody else may also have. This is how I solved it.

Prerequisites

I have configured HTTP proxy in standard mode using AD SSO for my internal network (192.180.1.0/24) and for my L2TP VPN pool (192.168.2.0/24).

LAN connected

Windows 10 client side proxy is configured to use the internal LAN IP address of the UTM (192.168.1.1) in Windows 10 Proxy settings under Settings->Network & Internet->Proxy. HTTP proxy port is the same as configured in the UTM HTTP proxy port setting.

Everything is working as expected.

L2TP/IPsec

Windows 10 client side proxy settings was a nut to crack. You have four different proxy settings in Windows 10 when using VPN connections!

  1. Windows settings: Network & Internet->Proxy which is configured for my internal LAN. Configured IP address is 192.168.1.1 (HTTP proxy port is the same as configured in the UTM HTTP proxy port setting) 
  2. Internet Explorer: Internet options->connections tab->LAN settings button. These settings should be the same as the above settings
  3. Windows settings: Network & Internet->VPN->Click the created VPN Connection and select advanced settings. Scroll down and you find manual proxy settings. I configured the IP address to UTM L2TP VPN Pool adress 192.168.2.1.(HTTP proxy port is the same as configured in the UTM HTTP proxy port setting)

I believed this should work. But it didn't. After hours of investigations I found the fourth setting

Internet Explorer: Internet options->connections tab->Select your created VPN Connection under Dail-up and Virtual Private Network settings, click Settings button. I configured the proxy server IP address to UTM L2TP VPN Pool address 192.168.2.1.(HTTP proxy port is the same as configured in the UTM HTTP proxy port setting)

And suddenly everything now works!

The quirkiness in this is that I assumed that the Windows VPN proxy settings should do it all, but apparently not.  It first started to work after configuring the created VPN connection in Internet Explorer.

Is this a Windows bug or a feature? What is the Windows VPN proxy settings for?

Using Windows 10 Pro, version 1607



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