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Please help! User->TOR->VPN workstation in VirtualBox

I tried to config Workstation13 under VirtualBox on MAC for User->TOR->VPN route.
But failed :frowning:

Could anybody please upload Workstation for VB configured to go User->TOR->VPN?
I would like to see what is the right configuration and understand where is my fault.
Or maybe not the whole VM but configuration files to copy to my workstation.

Or maybe somebody will try to check my settings via TeamViewer?
I’m ready to pay for your time, please help me!

Thanks!

Good day,

Sorry to tell you, but this isn’t possible, for the simple reason, that every VPN provider necessitates a slightly different configuration. Like @entr0py suggested, please go through all the steps, verifying everything is correct.

Have a nice day,

Ego

I tried 3 different VPN providers, one of them - my own OpenVPN Access Server on my hosting.
So, I think the problem is not in VPN provider but in my setup.
I have made all the setup steps twice with the same result :frowning: I double checked all resulting configuration files.

Workstation connects to VPN server via TCP , but it fails to handshake with VPN server.
Maybe somebody knows how to debug VPN communications on low level to understand what is going wrong?

Here is what “sudo service openvpn@openvpn status” says:

VPN status error after minute of handshaking -
Jul 17 21:03:00 host ovpn-openvpn[1542]: TCPv4_CLIENT link remote: [AF_INET]126.25.194.75:1712
Jul 17 21:04:00 host ovpn-openvpn[1542]: TLS Error: TLS key negotiation failed to occur within 60 seconds…vity)
Jul 17 21:04:00 host ovpn-openvpn[1542]: TLS Error: TLS handshake failed
Jul 17 21:04:00 host ovpn-openvpn[1542]: Fatal TLS error (check_tls_errors_co), restarting

And after some time is says -

Jul 17 23:02:13 host ovpn-openvpn[10720]: TCP connection established with [AF_INET]126.25.194.75:1712
Jul 17 23:02:13 host ovpn-openvpn[10720]: TCPv4_CLIENT link local: [undef]
Jul 17 23:02:13 host ovpn-openvpn[10720]: TCPv4_CLIENT link remote: [AF_INET]126.25.194.75:1712
Jul 17 23:02:16 host ovpn-openvpn[10720]: TLS_ERROR: BIO read tls_read_plaintext error: error:14090086:SSL routines:SSL3_GET_SERVER_CERTIFICATE:certificate verify failed
Jul 17 23:02:16 host ovpn-openvpn[10720]: TLS Error: TLS object -> incoming plaintext read error
Jul 17 23:02:16 host ovpn-openvpn[10720]: TLS Error: TLS handshake failed
Jul 17 23:02:16 host ovpn-openvpn[10720]: Fatal TLS error (check_tls_errors_co), restarting

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