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I have a Windows 2003 SBS box. It has 2 physical NIC's: WAN and LAN. The WAN is a public IP. The LAN is a simple 192.168.2.x subnet with Microsoft DHCP Server. Microsoft Routing and Remote Access Service is used to provide NAT to LAN. The box also runs VMware Server with a virtual machine running Windows XP. I want people to be able to VPN into the box, and connect to these virtual machines on the MSRDP port. I can VPN (PPTP) into the 2003 SBS box fine, as well as ping other machines on the LAN.

  • I can ping the VM from a physical workstation on the LAN and vice-versa.
  • I can ping the VPN client from the a physical workstation on the LAN and vice-versa.
  • I can ping the Server from the VPN client
  • EDIT: I cannot ping the VPN client from the Server!
  • I can ping the VM client from the Server console and vice-versa.
  • But I cannot ping the VPN client from the VM and vice-versa.

I was hoping to set up 2 or 3 Windows XP virtual machines on our only server, so that a couple of people can VPN then RDP in to work without having to leave a physical machine on in the office. You could this attempted set up a "poor mans terminal server".

On the 2003 SBS Server:-

C:\Documents and Settings\Administrator>route print

IPv4 Route Table
===========================================================================
Interface List
0x1 ........................... MS TCP Loopback interface
0x2 ...00 50 56 c0 00 08 ...... VMware Virtual Ethernet Adapter for VMnet8
0x3 ...00 50 56 c0 00 01 ...... VMware Virtual Ethernet Adapter for VMnet1
0x10004 ...00 53 45 00 00 00 ...... WAN (PPP/SLIP) Interface
0x10005 ...00 11 43 d4 69 13 ...... Broadcom NetXtreme Gigabit Ethernet
0x10006 ...00 11 43 d4 69 14 ...... Broadcom NetXtreme Gigabit Ethernet #2
===========================================================================
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0    81.123.144.22    81.123.144.21      1
    81.123.144.20  255.255.255.252    81.123.144.21    81.123.144.21      1
    81.123.144.21  255.255.255.255        127.0.0.1        127.0.0.1      1
   81.255.255.255  255.255.255.255    81.123.144.21    81.123.144.21      1
    86.135.78.235  255.255.255.255    81.123.144.22    81.123.144.21      1
   109.152.62.236  255.255.255.255    81.123.144.22    81.123.144.21      1
        127.0.0.0        255.0.0.0        127.0.0.1        127.0.0.1      1
      192.168.2.0    255.255.255.0      192.168.2.3      192.168.2.3      1
      192.168.2.3  255.255.255.255        127.0.0.1        127.0.0.1      1
     192.168.2.26  255.255.255.255     192.168.2.32     192.168.2.32      1
     192.168.2.28  255.255.255.255     192.168.2.32     192.168.2.32      1
     192.168.2.32  255.255.255.255        127.0.0.1        127.0.0.1     50
     192.168.2.50  255.255.255.255        127.0.0.1        127.0.0.1      1
    192.168.2.255  255.255.255.255      192.168.2.3      192.168.2.3      1
     192.168.10.0    255.255.255.0     192.168.10.1     192.168.10.1     20
     192.168.10.1  255.255.255.255        127.0.0.1        127.0.0.1     20
   192.168.10.255  255.255.255.255     192.168.10.1     192.168.10.1     20
     192.168.96.0    255.255.255.0     192.168.96.1     192.168.96.1     20
     192.168.96.1  255.255.255.255        127.0.0.1        127.0.0.1     20
   192.168.96.255  255.255.255.255     192.168.96.1     192.168.96.1     20
        224.0.0.0        240.0.0.0    81.123.144.21    81.123.144.21      1
        224.0.0.0        240.0.0.0      192.168.2.3      192.168.2.3      1
        224.0.0.0        240.0.0.0     192.168.10.1     192.168.10.1     20
        224.0.0.0        240.0.0.0     192.168.96.1     192.168.96.1     20
  255.255.255.255  255.255.255.255    81.123.144.21    81.123.144.21      1
  255.255.255.255  255.255.255.255      192.168.2.3      192.168.2.3      1
  255.255.255.255  255.255.255.255     192.168.10.1     192.168.10.1      1
  255.255.255.255  255.255.255.255     192.168.96.1     192.168.96.1      1
Default Gateway:     81.123.144.22
===========================================================================
Persistent Routes:
  None



C:\Documents and Settings\Administrator>ipconfig /all

Windows IP Configuration

   Host Name . . . . . . . . . . . . : 2003server
   Primary Dns Suffix  . . . . . . . : mycompany.local
   Node Type . . . . . . . . . . . . : Unknown
   IP Routing Enabled. . . . . . . . : Yes
   WINS Proxy Enabled. . . . . . . . : Yes
   DNS Suffix Search List. . . . . . : mycompany.local
                                       gateway.2wire.net

Ethernet adapter VMware Network Adapter VMnet8:

   Connection-specific DNS Suffix  . :
   Description . . . . . . . . . . . : VMware Virtual Ethernet Adapter for VMnet
8
   Physical Address. . . . . . . . . : 00-50-56-C0-00-08
   DHCP Enabled. . . . . . . . . . . : No
   IP Address. . . . . . . . . . . . : 192.168.10.1
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Default Gateway . . . . . . . . . :

Ethernet adapter VMware Network Adapter VMnet1:

   Connection-specific DNS Suffix  . :
   Description . . . . . . . . . . . : VMware Virtual Ethernet Adapter for VMnet
1
   Physical Address. . . . . . . . . : 00-50-56-C0-00-01
   DHCP Enabled. . . . . . . . . . . : No
   IP Address. . . . . . . . . . . . : 192.168.96.1
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Default Gateway . . . . . . . . . :

PPP adapter RAS Server (Dial In) Interface:

   Connection-specific DNS Suffix  . :
   Description . . . . . . . . . . . : WAN (PPP/SLIP) Interface
   Physical Address. . . . . . . . . : 00-53-45-00-00-00
   DHCP Enabled. . . . . . . . . . . : No
   IP Address. . . . . . . . . . . . : 192.168.2.32
   Subnet Mask . . . . . . . . . . . : 255.255.255.255
   Default Gateway . . . . . . . . . :
   NetBIOS over Tcpip. . . . . . . . : Disabled

Ethernet adapter LAN:

   Connection-specific DNS Suffix  . :
   Description . . . . . . . . . . . : Broadcom NetXtreme Gigabit Ethernet
   Physical Address. . . . . . . . . : 00-11-43-D4-69-13
   DHCP Enabled. . . . . . . . . . . : No
   IP Address. . . . . . . . . . . . : 192.168.2.50
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   IP Address. . . . . . . . . . . . : 192.168.2.3
   Subnet Mask . . . . . . . . . . . : 255.255.255.0
   Default Gateway . . . . . . . . . :
   DNS Servers . . . . . . . . . . . : 192.168.2.3
   Primary WINS Server . . . . . . . : 192.168.2.3

Ethernet adapter WAN:

   Connection-specific DNS Suffix  . : gateway.2wire.net
   Description . . . . . . . . . . . : Broadcom NetXtreme Gigabit Ethernet #2
   Physical Address. . . . . . . . . : 00-11-43-D4-69-14
   DHCP Enabled. . . . . . . . . . . : Yes
   Autoconfiguration Enabled . . . . : Yes
   IP Address. . . . . . . . . . . . : 81.123.144.21
   Subnet Mask . . . . . . . . . . . : 255.255.255.252
   Default Gateway . . . . . . . . . : 81.123.144.22
   DHCP Server . . . . . . . . . . . : 10.0.0.1
   DNS Servers . . . . . . . . . . . : 10.0.0.1
   Primary WINS Server . . . . . . . : 192.168.2.3
   NetBIOS over Tcpip. . . . . . . . : Disabled
   Lease Obtained. . . . . . . . . . : 25 February 2011 22:56:59
   Lease Expires . . . . . . . . . . : 25 February 2011 23:06:59




C:\Documents and Settings\Administrator>ping 192.168.2.11

Pinging 192.168.2.11 with 32 bytes of data:

Reply from 192.168.2.11: bytes=32 time<1ms TTL=128
Reply from 192.168.2.11: bytes=32 time<1ms TTL=128
Reply from 192.168.2.11: bytes=32 time<1ms TTL=128
Reply from 192.168.2.11: bytes=32 time<1ms TTL=128

On the VPN client:-

C:\>tracert 192.168.2.3  ## THIS IS THE SBS SERVER

Tracing route to 2003server.mycompany.local [192.168.2.3]
over a maximum of 30 hops:

  1    59 ms    58 ms    61 ms  2003server.mycompany.local [192.168.2.3]

Trace complete.

C:\>tracert 192.168.2.14  ## THIS IS A PHYSICAL LAN COMPUTER

Tracing route to ws2001.mycompany.local [192.168.2.14]
over a maximum of 30 hops:

  1    57 ms    57 ms    56 ms  192.168.2.32
  2    64 ms    63 ms    59 ms  ws2001.mycompany.local [192.168.2.14]

Trace complete.

C:\>tracert 192.168.2.11  ## THIS IS THE VM

Tracing route to ws2009.mycompany.local [192.168.2.11]
over a maximum of 30 hops:

  1    69 ms    58 ms    56 ms  192.168.2.32
  2     *        *        *     Request timed out.
  3     *        *        *     Request timed out.
(the rest is omitted, all timeouts)

IPv4 Route Table
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0          5.0.0.1     5.131.104.16   9256
          0.0.0.0          0.0.0.0      192.168.2.1    192.168.2.104     25
          5.0.0.0        255.0.0.0         On-link      5.131.104.16   9256
     5.131.104.16  255.255.255.255         On-link      5.131.104.16   9256
    5.255.255.255  255.255.255.255         On-link      5.131.104.16   9256
    81.149.144.21  255.255.255.255      192.168.2.1    192.168.2.104     26
        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
      192.168.2.0    255.255.255.0         On-link     192.168.2.104    281
      192.168.2.0    255.255.255.0     192.168.2.32     192.168.2.23     26
     192.168.2.23  255.255.255.255         On-link      192.168.2.23    281
    192.168.2.104  255.255.255.255         On-link     192.168.2.104    281
    192.168.2.255  255.255.255.255         On-link     192.168.2.104    281
     192.168.56.0    255.255.255.0         On-link      192.168.56.1    276
     192.168.56.1  255.255.255.255         On-link      192.168.56.1    276
   192.168.56.255  255.255.255.255         On-link      192.168.56.1    276
        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      192.168.56.1    276
        224.0.0.0        240.0.0.0         On-link      5.131.104.16   9256
        224.0.0.0        240.0.0.0         On-link     192.168.2.104    281
  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      192.168.56.1    276
  255.255.255.255  255.255.255.255         On-link      5.131.104.16   9256
  255.255.255.255  255.255.255.255         On-link     192.168.2.104    281
  255.255.255.255  255.255.255.255         On-link      192.168.2.23    281
===========================================================================
Persistent Routes:
  Network Address          Netmask  Gateway Address  Metric
          0.0.0.0          0.0.0.0          5.0.0.1  Default
===========================================================================

On the VM:-

C:\Documents and Settings\Administrator>route print
===========================================================================
Interface List
0x1 ........................... MS TCP Loopback interface
0x10003 ...00 0c 29 dc a2 c1 ...... VMware Accelerated AMD PCNet Adapter
===========================================================================
===========================================================================
Active Routes:
Network Destination        Netmask          Gateway       Interface  Metric
          0.0.0.0          0.0.0.0      192.168.2.3    192.168.2.11       10
        127.0.0.0        255.0.0.0        127.0.0.1       127.0.0.1       1
      192.168.2.0    255.255.255.0     192.168.2.11    192.168.2.11       10
     192.168.2.11  255.255.255.255        127.0.0.1       127.0.0.1       10
    192.168.2.255  255.255.255.255     192.168.2.11    192.168.2.11       10
        224.0.0.0        240.0.0.0     192.168.2.11    192.168.2.11       10
  255.255.255.255  255.255.255.255     192.168.2.11    192.168.2.11       1
Default Gateway:       192.168.2.3
===========================================================================
Persistent Routes:
  None

C:\Documents and Settings\Administrator>tracert 192.168.2.23

Tracing route to 192.168.2.23 over a maximum of 30 hops

  1     *        *        *     Request timed out.
  2     *     ^C
C:\Documents and Settings\Administrator>tracert 192.168.2.3

Tracing route to 2003server.mycompany.local [192.168.2.3]
over a maximum of 30 hops:

  1     1 ms    <1 ms    <1 ms  2003server.mycompany.local [192.168.2.3]

Trace complete.

C:\Documents and Settings\Administrator>tracert 192.168.2.14

Tracing route to ws2001.mycompany.local [192.168.2.14]
over a maximum of 30 hops:

  1    <1 ms    <1 ms    <1 ms  ws2001.mycompany.local [192.168.2.14]

Trace complete.

C:\Documents and Settings\Administrator>ipconfig /all

Windows IP Configuration

        Host Name . . . . . . . . . . . . : vm1
        Primary Dns Suffix  . . . . . . . : MyCompany.local
        Node Type . . . . . . . . . . . . : Hybrid
        IP Routing Enabled. . . . . . . . : No
        WINS Proxy Enabled. . . . . . . . : No
        DNS Suffix Search List. . . . . . : MyCompany.local
                                            mycompany.local

Ethernet adapter Local Area Connection:

        Connection-specific DNS Suffix  . : mycompany.local
        Description . . . . . . . . . . . : VMware Accelerated AMD PCNet Adapter

        Physical Address. . . . . . . . . : 00-0C-29-DC-A2-C1
        Dhcp Enabled. . . . . . . . . . . : Yes
        Autoconfiguration Enabled . . . . : Yes
        IP Address. . . . . . . . . . . . : 192.168.2.11
        Subnet Mask . . . . . . . . . . . : 255.255.255.0
        Default Gateway . . . . . . . . . : 192.168.2.3
        DHCP Server . . . . . . . . . . . : 192.168.2.3
        DNS Servers . . . . . . . . . . . : 192.168.2.3
        Primary WINS Server . . . . . . . : 192.168.2.3
        Lease Obtained. . . . . . . . . . : 25 February 2011 22:23:31
        Lease Expires . . . . . . . . . . : 05 March 2011 22:23:31
share|improve this question
    
Can you throw WireShark on your SBS 2003 server and sniff traffic (dst.ip == 192.168.2.11)? –  gravyface Feb 28 '11 at 15:09
1  
And you definitely want a bridged configuration for VMServer. –  gravyface Feb 28 '11 at 15:21
    
It's a production server - sorry, I do agree that Wireshark would help, but I don't want to risk that, installing VMware Server was scary enough. –  servermanfail Mar 1 '11 at 18:52
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3 Answers

In this configuration its generally best to make sure your vm's are using bridged ethernet connections with the LAN interface, this way they should basically act like LAN client workstations.

Also worth ruling out, the subnets of either your vpn or vm's arent the same as your local IP at the remote end of the vpn? If so you may have some routing issues

share|improve this answer
    
Yes, my vm's are bridged to LAN ethernet (verified). Yes, it feels like a routing issue, but I need some route add commands maybe? –  servermanfail Mar 1 '11 at 18:51
    
if the vm's are on the same IP subnet as the lan clients then no they shouldnt, if they have seperate subnets then probably –  anthonysomerset Mar 1 '11 at 19:37
add comment

It sounds like you probably don't have your VM's patched in with the right kind of networking. Did you use a bridge device or a nat device? Did you append the to wan or lan interface on the host? Did you setup port forwarding right? If you give a few more implementation details I think we're more likly to be able to find which bit of wiring is missing.

share|improve this answer
    
I tried Bridged and NAT. I tried appending virtual NIC to RRAS>NAT>LAN. I can't setup port forwarding, because it won't let me on LAN interfaces. I'll get you some more info soon ish. Thanks for trying to help. –  servermanfail Feb 24 '11 at 17:29
    
I updated the question. –  servermanfail Feb 26 '11 at 18:58
add comment

Have a read of this. If it doesnt help, it will explain the vm networking setup.

http://communities.vmware.com/thread/83874

May point you in a new direction with hopefully a successful outcome

Can you run a tracert from the VPN client to the virtual host? and vice-versus. What is the outcome?

share|improve this answer
    
I've updated question to supply tracert's you requested. But that thread didn't help me. Can't be firewall, can it? I can't turn Firewall on the Host OS off due to Group Policies, but it allows ICMP Ping, and can be pinged from the server. –  servermanfail Mar 1 '11 at 19:19
    
@servermanfail: it seems strange that you are only getting one hop from the vpn client to the sbs server on 192.168.2.3. You are testing this from outside the network arent you? When you get a vpn connection, what is your subnet mask for you PPP adapter. –  IanN Mar 1 '11 at 21:19
    
255.255.255.255 –  servermanfail Mar 2 '11 at 21:34
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