Why is my OpenVPN Client not connecting to the server? Amazon EC2 Windows

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You can ignore the thing about port forwarding. That's in a situation where you have the OpenVPN server behind some sort of router. In that case, you'll have to forward 1194/udp traffic to the server.

Can you make sure the clocks on both machines are in sync?

The other thing would be to double check the EC2 Security Groups to make sure you're allowing incoming 1194/udp traffic.

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npiani
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npiani

Updated on September 18, 2022

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  • npiani
    npiani over 1 year

    I have been trying to set up OpenVPN on an Amazon EC2 instance running Windows 2008 SQL Server. After following several tutorials, I have been able to get the server running. Here is my server conf file:

    ## server.ovpn ##
    
    port 1194
    
    proto udp
    
    dev tun
    
    ca xxxx.crt
    
    cert xxxx.crt
    
    key xxxx.key
    
    dh dh2048.pem
    
    server 10.8.0.0 255.255.255.0
    
    ifconfig-pool-persist ipp.txt
    
    keepalive 10 120
    
    comp-lzo
    
    max-clients 100
    
    persist-key
    
    persist-tun
    
    status openvpn-status.log
    
    verb 3
    

    But when setting up the client side, the connection times out giving the following error: TLS key negotiation failed to occur within 60 seconds (check your network connectivity)

    I have tried a TCP connection instead to no avail, and I opened the 1194 port on the EC2 firewall. Both internally and on the security settings of the EC2 instance.

    The OpenVPN HOWTO says to make sure I am are using a correct port forward rule on the server's gateway firewall. But I am not sure what that means exactly.

    Thanks in advance. I will post my client conf file as well just in case.

    client
    
    dev tun
    
    proto udp
    
    remote "Amazon instance Elastic IP" 1194
    
    resolv-retry infinite
    
    nobind
    
    persist-key
    
    persist-tun
    
    ca xxxx.crt
    
    cert xxxx.crt
    
    key xxxx.key
    
    ns-cert-type server
    
    comp-lzo
    
    verb 3
    
  • npiani
    npiani about 12 years
    Thank you cjc, The clocks were not in sync and that seemed to be the issue.