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I have set up an OpenVPN server on my Debian Wheezy machine. When I try to connect from my Windows 7 client machine, I receive some message which I am not able to decipher.

I would be very grateful if someone can give me tips necessary for solving my connection problem. What is the reason that causes my client to fail ? :?

Please note that my router which my Debian machine is connected to has enabled Virtual Server NAT and port forward 443 to my local eth0 ip address 192.168.1.5 .

This is my OpenGUI message

Sun Sep 15 23:52:07 2013 MANAGEMENT: TCP Socket listening on [AF_INET]127.0.0.1:25340
Sun Sep 15 23:52:07 2013 Need hold release from management interface, waiting...
Sun Sep 15 23:52:08 2013 MANAGEMENT: Client connected from [AF_INET]127.0.0.1:25340
Sun Sep 15 23:52:08 2013 MANAGEMENT: CMD 'state on'
Sun Sep 15 23:52:08 2013 MANAGEMENT: CMD 'log all on'
Sun Sep 15 23:52:08 2013 MANAGEMENT: CMD 'hold off'
Sun Sep 15 23:52:08 2013 MANAGEMENT: CMD 'hold release'
Sun Sep 15 23:52:08 2013 WARNING: No server certificate verification method has been enabled. See http://openvpn.net/howto.html#mitm for more info.
Sun Sep 15 23:52:08 2013 Socket Buffers: R=[8192->8192] S=[8192->8192]
Sun Sep 15 23:52:08 2013 Attempting to establish TCP connection with
[AF_INET]100.72.58.214:443 Sun Sep 15 23:52:08 2013 MANAGEMENT: >STATE:1379260328,TCP_CONNECT,,,
Sun Sep 15 23:52:29 2013 TCP: connect to [AF_INET]100.72.58.214:443 failed, will try again in 5 seconds: Connection timed out (WSAETIMEDOUT)
Sun Sep 15 23:52:34 2013 MANAGEMENT: >STATE:1379260354,TCP_CONNECT,,,

My server.conf

local 192.168.1.5
port 443
proto tcp-server
dev tun0

ca /etc/openvpn/ca.crt
cert /etc/openvpn/server.crt
key /etc/openvpn/server.key
dh /etc/openvpn/dh1024.pem

server 10.9.8.0 255.255.255.0

keepalive 10 120

comp-lzo persist-key persist-tun

verb 3 client-to-client log-append /var/log/openvpn

My client.ovnp

client dev tun0 proto tcp

lport 51 rport 443

remote 100.72.58.214

resolv-retry infinite

ca ca.crt cert client.crt key client.key

comp-lzo persist-key persist-tun

verb 3

rc.local

iptables -A FORWARD -m state --state RELATED,ESTABLISHED -j ACCEPT
iptables -A FORWARD -s 10.9.8.0/24 -j ACCEPT
iptables -A FORWARD -j REJECT
iptables -t nat -A POSTROUTING -s 10.9.8.0/24 -o eth0 -j MASQUERADE

/etc/init.d/dnsmasq restart

exit 0

I have added to the end of dnsmasq.conf file:

listen-address 127.0.0.1,10.9.8.0
bind-interfaces

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1 Answer 1

There are some added security settings in Windows 7 that makes it difficult to conner with openvpn. What I did was to run the openvpn client as admin.

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