Windows – SSTP on Windows 2008 cannot ping in either direction

routingsstpvpnwindows

I have the following setting going on.

Server: Configured windows 2008 server as AD, DHCP, DNS, CA and RRAS. To make long story short, RRAS can accept SSTP connection and clients get connected fine. Clients get IP address.

Client: Windows 7 OS

Configuration:

I have a linux firewall at the perimeter. The port has been opened to forward 443 to an internal IP address and port on the RRAS server.

The private network is on a 10.100.0.0/16 subnet.

RRAS server has 2 NIC. NIC1=10.100.85.15 and NIC2=10.100.85.16. NIC2 is accepting SSTP connections from the public internet. The adapter settings on NIC2 only has the static IP and subnet. No gateway and DNS servers are configured on NIC2 (this I did based on something I read somewhere regarding setting up PPTP on Windows 2003). NIC1 has the top priority out of the 2 NICs.

RRAS has been setup for VPN only (no NAT). The IP address allocation is static and it is from the pool of 10.100.77.250 to 10.100.77.254 (the same subnet as the private network).

I have allowed ICMP any on either direction in the inbound and outbound filters.

Windows Firewall has been configured to allow pretty much everything – and then at this configuration I have turned off the Windows Firewall Service.

I have not added any static routes to RRAS.

As mentioned earlier, the VPN client is able to connect to RRAS over SSTP and get and IP address. Client is able to ping the RRAS gateway (10.100.77.250), NIC1 and NIC2.

Issue:

The client cannot ping to any machine other than the RRAS server

More Debug Information:

I installed Microsoft Network Monitor on RRAS server to monitor the ICMP packets. I do see the ICMP request going from client (say 10.100.77.251) to RRAS to destination server (say 10.100.20.10), and 10.100.20.10 responds with ICMP reply back to 10.100.77.251 with ethernet address of NIC1. At this point, here is the routing table from the RRAS server.

===========================================================================
Interface List
 12 ...7a dd d0 eb af 8c ...... Citrix PV Ethernet Adapter #0
 13 ...7e ab 6f 21 e8 30 ...... Citrix PV Ethernet Adapter #1
 26 ........................... RAS (Dial In) Interface
  1 ........................... Software Loopback Interface 1
 14 ...00 00 00 00 00 00 00 e0  isatap.{BCF77165-229C-410C-AE43-D71B6D902F6A}
 27 ...00 00 00 00 00 00 00 e0  Microsoft ISATAP Adapter
 15 ...00 00 00 00 00 00 00 e0  isatap.{4705FD1E-0998-43A4-9EBE-46776B90B205}
===========================================================================

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0       10.100.0.1     10.100.85.15    356
       10.100.0.0      255.255.0.0         On-link      10.100.85.15    356
       10.100.0.0      255.255.0.0         On-link      10.100.85.16    358
    10.100.77.253  255.255.255.255    10.100.77.253    10.100.77.254     31
    10.100.77.254  255.255.255.255         On-link     10.100.77.254    286
     10.100.85.15  255.255.255.255         On-link      10.100.85.15    356
     10.100.85.16  255.255.255.255         On-link      10.100.85.16    358
   10.100.255.255  255.255.255.255         On-link      10.100.85.15    356
   10.100.255.255  255.255.255.255         On-link      10.100.85.16    358
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    306
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    306
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link      10.100.85.16    358
        224.0.0.0        240.0.0.0         On-link      10.100.85.15    356
        224.0.0.0        240.0.0.0         On-link     10.100.77.254    286
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    306
  255.255.255.255  255.255.255.255         On-link      10.100.85.16    358
  255.255.255.255  255.255.255.255         On-link      10.100.85.15    356
  255.255.255.255  255.255.255.255         On-link     10.100.77.254    286
===========================================================================
Persistent Routes:
  Network Address          Netmask  Gateway Address  Metric
          0.0.0.0          0.0.0.0       10.100.0.1  Default 
          0.0.0.0          0.0.0.0       10.100.0.1  Default 
          0.0.0.0          0.0.0.0       10.100.0.1  Default 
===========================================================================

IPv6 Route Table
===========================================================================
Active Routes:
 If Metric Network Destination      Gateway
  1    306 ::1/128                  On-link
 13    266 fe80::/64                On-link
 12    266 fe80::/64                On-link
 12    266 fe80::a8b1:77f:5eb0:d5a8/128
                                    On-link
 13    266 fe80::f8a0:2a9d:bee9:e688/128
                                    On-link
  1    306 ff00::/8                 On-link
 13    266 ff00::/8                 On-link
 12    266 ff00::/8                 On-link
===========================================================================
Persistent Routes:
  None

I know there is some routing issue…and I have tried all combinations to insert a route add in the RRAS but nothing works. Any help is greatly appreciated.

Update: Converted the AD machine to a single NIC configuration. Here is the routing table on client and RRAS when the Client is connected.

===========================================================================
Interface List
 12 ...7a dd d0 eb af 8c ...... Citrix PV Ethernet Adapter #0
 22 ........................... RAS (Dial In) Interface
  1 ........................... Software Loopback Interface 1
 23 ...00 00 00 00 00 00 00 e0  Microsoft ISATAP Adapter
 14 ...00 00 00 00 00 00 00 e0  isatap.{4705FD1E-0998-43A4-9EBE-46776B90B205}
===========================================================================

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0       10.100.0.1     10.100.85.15    356
       10.100.0.0      255.255.0.0         On-link      10.100.85.15    356
    10.100.77.252  255.255.255.255    10.100.77.252    10.100.77.254     31
    10.100.77.254  255.255.255.255         On-link     10.100.77.254    286
     10.100.85.15  255.255.255.255         On-link      10.100.85.15    356
   10.100.255.255  255.255.255.255         On-link      10.100.85.15    356
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    306
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    306
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link      10.100.85.15    356
        224.0.0.0        240.0.0.0         On-link     10.100.77.254    286
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    306
  255.255.255.255  255.255.255.255         On-link      10.100.85.15    356
  255.255.255.255  255.255.255.255         On-link     10.100.77.254    286
===========================================================================
Persistent Routes:
  Network Address          Netmask  Gateway Address  Metric
          0.0.0.0          0.0.0.0       10.100.0.1  Default 
          0.0.0.0          0.0.0.0       10.100.0.1  Default 
          0.0.0.0          0.0.0.0       10.100.0.1  Default 
===========================================================================

IPv6 Route Table
===========================================================================
Active Routes:
 If Metric Network Destination      Gateway
  1    306 ::1/128                  On-link
 12    266 fe80::/64                On-link
 12    266 fe80::a8b1:77f:5eb0:d5a8/128
                                    On-link
  1    306 ff00::/8                 On-link
 12    266 ff00::/8                 On-link
===========================================================================
Persistent Routes:
  None

Client

===========================================================================
Interface List
 23...........................VPN
 10...08 00 27 e9 14 91 ......Intel(R) PRO/1000 MT Desktop Adapter
  1...........................Software Loopback Interface 1
 11...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter
 13...00 00 00 00 00 00 00 e0 Microsoft ISATAP Adapter #2
===========================================================================

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0    192.168.123.2   192.168.123.15     10
         10.0.0.0        255.0.0.0    10.100.77.254    10.100.77.252     11
    10.100.77.252  255.255.255.255         On-link     10.100.77.252    266
        127.0.0.0        255.0.0.0         On-link         127.0.0.1    306
        127.0.0.1  255.255.255.255         On-link         127.0.0.1    306
  127.255.255.255  255.255.255.255         On-link         127.0.0.1    306
    192.168.123.0    255.255.255.0         On-link    192.168.123.15    266
   192.168.123.15  255.255.255.255         On-link    192.168.123.15    266
  192.168.123.255  255.255.255.255         On-link    192.168.123.15    266
  216.218.195.214  255.255.255.255    192.168.123.2   192.168.123.15     11
        224.0.0.0        240.0.0.0         On-link         127.0.0.1    306
        224.0.0.0        240.0.0.0         On-link    192.168.123.15    266
        224.0.0.0        240.0.0.0         On-link     10.100.77.252    266
  255.255.255.255  255.255.255.255         On-link         127.0.0.1    306
  255.255.255.255  255.255.255.255         On-link    192.168.123.15    266
  255.255.255.255  255.255.255.255         On-link     10.100.77.252    266
===========================================================================
Persistent Routes:
  None

IPv6 Route Table
===========================================================================
Active Routes:
 If Metric Network Destination      Gateway
  1    306 ::1/128                  On-link
  1    306 ff00::/8                 On-link
===========================================================================
Persistent Routes:
  None

Best Answer

Two things I noticed. 1) AD should never have more than one NIC. A multi-homed DC is not supported by MS. But I don't think that's causing your problem. 2) You turned off the Windows Firewall Service. Probably not a good idea. Try turning the service back on and running the following command to disable the profiles.

Netsh advfirewall set allprofiles state off

I'm still not sure if this will solve your problem, but those two things jumped out at me.

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