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So I've configured openvpn to another server and I can now successfully start the process on ubuntu and it says I am connected. However, if I try to SSH to other servers or access privileged websites (only within the VPN), I don't have any luck. Is there usually any further I need to do to get traffic tunnelled through the openvpn service when it is running?

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Let us see your log-files, please.

Have you enabled IP forwarding? Masquerade in iptables of server? If not, I think, you should look this manual, as I did- https://wiki.debian.org/OpenVPN#Forward_traffic_via_VPN

I pushed my traffic by these commands:

  1. Edit in /etc/sysctl.conf - net.ipv4.ip_forward = 1
  2. IPtables rules:

    iptables -A FORWARD -i eth0 -o tun0 -m state --state ESTABLISHED,RELATED -j ACCEPT
    iptables -A FORWARD -s 10.10.5.0/24 -o eth0 -j ACCEPT
    iptables -t nat -A POSTROUTING -s 10.10.5.0/24 -o eth0 -j MASQUERADE
    

Where 10.10.5.0/24 is your internal network, which you defined in server.conf on this line

server 10.10.5.0 255.255.255.0

Also, add this to your server.conf file

# If you want push all your client's traffic through VPN
push "redirect-gateway" def1 bypass-dhcp"

#Or limit by ip-addres of destination
push "route 74.125.224.72 255.255.255.255"
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