Windows 7 client fails to connect to Debian OpenVPN server












0















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










share|improve this question





























    0















    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










    share|improve this question



























      0












      0








      0








      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










      share|improve this question
















      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







      openvpn






      share|improve this question















      share|improve this question













      share|improve this question




      share|improve this question








      edited Sep 16 '13 at 6:39









      BlueBerry - Vignesh4303

      5,498205078




      5,498205078










      asked Sep 16 '13 at 5:26









      Nikola RadakovicNikola Radakovic

      112




      112






















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          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.






          share|improve this answer























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            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.






            share|improve this answer




























              0














              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.






              share|improve this answer


























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                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.






                share|improve this answer













                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.







                share|improve this answer












                share|improve this answer



                share|improve this answer










                answered Mar 23 '14 at 7:42









                SifunguruxSifungurux

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