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Started using OpenVPN on my desktop computer and monitored the traffic with Microsoft network monitor. What I noticed, is that when the openvpn session is initialized, only connections established after this point are routed through the VPN. That is to say I had to restart Skype to get it to route traffic through OpenVPN. is there a way to make it terminate connections and re-establish them once the tunnel is up?

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OpenVPN creates a new interface for connections to go through, it doesn't override all connections that exist. In other words, it becomes an 'optional' connection. This can be important because you might need to use local network resources without the VPN.

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