When establishing a VPN incoming connection on Windows Server 2008 (Web Edition), the primary obstacle is the absence of RRAS (Routing and Remote Access Service). This limitation prevents automatic NAT configuration for routing all client traffic through the VPN tunnel. Let's examine a working solution using built-in Windows features and manual routing configuration.

First, enable the VPN incoming connection feature:

netsh routing ip nat install
netsh routing ip nat add interface "Internal" full
netsh routing ip nat set interface "External" mode=full

Since RRAS isn't available, we'll configure NAT manually through command line:

:: Enable IP forwarding
reg add HKLM\SYSTEM\CurrentControlSet\Services\Tcpip\Parameters /v IPEnableRouter /t REG_DWORD /d 1 /f

:: Configure NAT (replace 'Ethernet' with your external interface name)
netsh interface ipv4 set interface "Ethernet" forwarding=enabled
netsh interface ipv4 add route 0.0.0.0/0 "Ethernet" %gateway% store=active

For PPTP setup (works without RRAS):

:: Enable PPTP ports
netsh firewall set portopening TCP 1723 "VPN PPTP"
netsh firewall set portopening protocol=GRE

:: Configure VPN user permissions
net user vpnuser * /add
net localgroup "Remote Desktop Users" vpnuser /add

After connecting, ensure client pushes all traffic:

:: On Windows client
rasphone -f "Your VPN Connection"
:: Or for persistent configuration:
addVPNConnection -Name "SecureVPN" -ServerAddress your.server.ip -TunnelType PPTP -SplitTunneling $false

If manual configuration proves complex, consider these open-source alternatives:

• SoftEther VPN Server (supports L2TP/IPSec)
• OpenVPN with Windows tap driver
• Pritunl for enterprise-grade setup

When traffic isn't routing properly:

1. Verify NAT translation: netsh routing ip nat show interface
2. Check default gateway: route print
3. Test basic connectivity: ping 8.8.8.8 -S [VPN_IP]

When setting up a VPN incoming connection on Windows Server 2008 (Web Edition), the default configuration only allows access to the server itself - not internet traffic routing. This occurs because:

• The server lacks RRAS (Routing and Remote Access Service)
• NAT and IP forwarding aren't enabled by default
• PPTP/L2TP connections don't automatically configure routing tables

Here's how to transform your Windows Server 2008 into a full-tunnel VPN gateway:

1. Enable IP Forwarding

reg add HKLM\SYSTEM\CurrentControlSet\Services\Tcpip\Parameters /v IPEnableRouter /t REG_DWORD /d 1 /f

2. Configure NAT Manually

Create a batch script (vpn_nat.bat) with these commands:

@echo off
netsh interface ipv4 set interface "Local Area Connection" forwarding=enabled
netsh interface ipv4 set interface "Internal" forwarding=enabled
netsh interface ipv4 add route 0.0.0.0/0 "Local Area Connection" 192.168.1.1
netsh interface ipv4 add portproxy v4tov4 listenport=8080 connectaddress=127.0.0.1 connectport=80

For Web Server 2008 without RRAS, consider these free alternatives:

SoftEther VPN Server

# Sample SoftEther configuration for full-tunnel:
declare SecureNAT
{
    bool Disabled false
    bool SaveLog false
    bool DHCPEnabled true
    bool NATEnabled true
    string VirtualDHCP 192.168.30.1/24
    string VirtualDNS 8.8.8.8
    string VirtualRouter 192.168.30.1
}

After setup, verify with these commands:

ping 8.8.8.8 -S [VPN_CLIENT_IP]
tracert www.google.com
route print

• No internet access: Check firewall rules for ICMP and DNS
• Slow speeds: Adjust MTU size on both server and client
• DNS leaks: Force DNS through VPN with netsh interface ip set dns name="VPN" source=static addr=8.8.8.8

For production environments:

# Block non-VPN traffic (Windows Firewall)
netsh advfirewall firewall add rule name="Block Non-VPN" dir=out action=block remoteip=!192.168.30.0/24