VPN to Server-side subnets

thespecial_one

First of all thank to all of you.

I'm trying to build a VPN connection as explained in the picture (I've made a link to it as I can't upload the image here http://dl.dropboxusercontent.com/u/96485834/VPNproblema.jpg ). VPN from Debian laptop client to Linux Debian Server works perfectly and I can share files via samba. But from the same laptop (same config file) with Windows Vista it says connection is established, tunnel rised and IP 10.20.30.6 assigned to client but I can't ping either see share folders with 10.10.10.0/24 Debian Server network.

2nd question: I would like to know if it is possible to build the VPN connection from Debian/Vista notrebook (client) to Windows Server 2012 virtual machine network and access virtual domain prueba.local (192.168.200.0 /24)?

Following I paste my server (core2quad.conf) and my client (debian.conf or conf.ovpn) files:

SERVER

port 1194
proto udp
dev tun
persist-key
persist-tun
status /etc/openvpn/openvpn-status.log
ca /etc/openvpn/ca.crt
cert /etc/openvpn/core2quad.crt
key /etc/openvpn/core2quad.key
dh /etc/openvpn/dh1024.pem
server 10.20.30.0 255.255.255.0
ifconfig-pool-persist /etc/openvpn/ipp.txt
push "route 192.168.200.0 255.255.255.0"
push "route 10.20.30.0 255.255.255.0"
cipher AES-128-CBC # AES
comp-lzo
keepalive 10 120
tun-mtu 1500

__________________________________________________
CLIENT
__________________________________________________

client
dev tun
proto udp
remote X.X.X.X 1194 ## public address
float
resolv-retry infinite
nobind
persist-key
persist-tun
ca ca.crt
cert debian.crt
key debian.key
ns-cert-type server
cipher AES-128-CBC # AES
comp-lzo
tun-mtu 1500
keepalive 10 120
verb 4

Thanks again for your time and interest.

brendan

question the first, it seems that the windows client is not getting the route settings you are pushing from the client. check the openvpn client logs on the windows machine. it likely has errors about not being able to add routes. that is because the openvpn client needs to be run as an administrator ID. i usually log in as myself and right-click -> Run As Administrator.

question the second, i see no reason you cant do what you are looking to in that scenario. two points to pay attention to: the point above about getting routing pushed to the client without errors, and second, making sure that routing from the vpn box to the remote networks is in place.

a note on your config. you are stating that your servers IP is 10.20.30.0 on a /24 network. in most cases .0 is the network identifier address and is not valid for assignment. try picking .1 or some other IP in the range. in terms of the routes you are pushing, the 10.20.30.0 network is considered locally connected to the vpn client and likely is not needed as a pushed config to the client.

thespecial_one

Thank you for your answer Brendan.

In the Vista partition (notebook) I just have one (default) user installed the Administrator (as I don't actually use that system very often). Anyway, I have tried tu Run as Administrator but it doesn't connect at all. Not even gives me IP address 10.20.30.6 which would be normal.
The client log file says this:

"Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:00:50+0200 [MyOMIClient,0,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:00:49 +0000] "POST /RPC2 HTTP/1.1" 200 490 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:00:52+0200 [MyOMIClient,0,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:00:51 +0000] "POST /RPC2 HTTP/1.1" 200 401 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:00:52+0200 [HTTPChannel,1,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:00:51 +0000] "POST /RPC2 HTTP/1.1" 200 471 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:01:02+0200 [-] 127.0.0.1 - - [28/May/2013:19:01:01 +0000] "POST /RPC2 HTTP/1.1" 200 138 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:01:03+0200 [MyOMIClient,0,127.0.0.1] OMI Cancel pending deferred ['exit']
2013-05-28 21:01:03+0200 [-] 127.0.0.1 - - [28/May/2013:19:01:02 +0000] "POST /RPC2 HTTP/1.1" 200 402 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:01:03+0200 [-] OpenVPN debian_conf_p9985 stop: process stopped with exit code 0
2013-05-28 21:01:03+0200 [-] 127.0.0.1 - - [28/May/2013:19:01:02 +0000] "POST /RPC2 HTTP/1.1" 200 216 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:01:03+0200 [HTTPChannel,1,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:01:02 +0000] "POST /RPC2 HTTP/1.1" 200 2023 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:01:03+0200 [HTTPChannel,0,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:01:03 +0000] "POST /RPC2 HTTP/1.1" 200 2023 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:01:09+0200 [HTTPChannel,1,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:01:08 +0000] "POST /RPC2 HTTP/1.1" 200 2023 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:01:10+0200 [HTTPChannel,0,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:01:10 +0000] "POST /RPC2 HTTP/1.1" 200 2023 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:05:03+0200 [HTTPChannel,2,127.0.0.1] OpenVPN debian_conf_p9985 instantiated
2013-05-28 21:05:03+0200 [HTTPChannel,2,127.0.0.1] pyovpn.client.vpncli.MyOMIServer starting on 43380
2013-05-28 21:05:03+0200 [HTTPChannel,2,127.0.0.1] Starting factory <pyovpn.client.vpncli.MyOMIServer instance at 0x02951AD0>
2013-05-28 21:05:04+0200 [-] (Port 43380 Closed)
2013-05-28 21:05:04+0200 [-] Stopping factory <pyovpn.client.vpncli.MyOMIServer instance at 0x02951AD0>
2013-05-28 21:05:04+0200 [MyOMIClient,0,127.0.0.1] OpenVPN start: name='debian_conf_p9985' sev='info' msg='process started successfully'
2013-05-28 21:05:04+0200 [MyOMIClient,0,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:05:03 +0000] "POST /RPC2 HTTP/1.1" 200 167 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:05:04+0200 [HTTPChannel,2,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:05:03 +0000] "POST /RPC2 HTTP/1.1" 200 402 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:05:04+0200 [MyOMIClient,0,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:05:03 +0000] "POST /RPC2 HTTP/1.1" 200 401 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:05:04+0200 [HTTPChannel,2,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:05:04 +0000] "POST /RPC2 HTTP/1.1" 200 470 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:05:11+0200 [MyOMIClient,0,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:05:11 +0000] "POST /RPC2 HTTP/1.1" 200 470 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"
2013-05-28 21:05:19+0200 [MyOMIClient,0,127.0.0.1] 127.0.0.1 - - [28/May/2013:19:05:19 +0000] "POST /RPC2 HTTP/1.1" 200 470 "-" "Mozilla/5.0 (Windows; U; Windows NT 6.0; en-US; rv:1.9.2pre) Gecko/20100322 Prism/1.0b4 OpenVPN/1.5.0"

Route PRINT (client):
IPv4 Tabla de enrutamiento
===========================================================================
Rutas activas:
Destino de red M scara de red Puerta de enlace Interfaz Mtrica
0.0.0.0 0.0.0.0 192.168.1.1 192.168.1.112 40
127.0.0.0 255.0.0.0 En v¡nculo 127.0.0.1 306
127.0.0.1 255.255.255.255 En v¡nculo 127.0.0.1 306
127.255.255.255 255.255.255.255 En v¡nculo 127.0.0.1 306
192.168.1.0 255.255.255.0 En v¡nculo 192.168.1.112 296
192.168.1.112 255.255.255.255 En v¡nculo 192.168.1.112 296
192.168.1.255 255.255.255.255 En v¡nculo 192.168.1.112 296
224.0.0.0 240.0.0.0 En v¡nculo 127.0.0.1 306
224.0.0.0 240.0.0.0 En v¡nculo 192.168.1.112 296
255.255.255.255 255.255.255.255 En v¡nculo 127.0.0.1 306
255.255.255.255 255.255.255.255 En v¡nculo 192.168.1.112 296
===========================================================================
Rutas persistentes:
Ninguno

Necesito ayuda por favor.
Gracias.