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There is VPS with OpenVPN and i2prouter on board. It is possible to send all traffic from local machine via VPN (using OpenVPN client). When VPN is off, I can forward localhost:4444 (for i2p proxy) to VPS via SSH and surf .i2p.

Desired situation: i2p proxy works when VPN is on and no SHH port forwarding. Any recommendations to do it?

I'm not familiar with VPN architecture, will thank for all answers.

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The connection between the vps' router and your vps would be completely in the clear and visible to anyone plugging in a packet sniffer on the hosting systems Ethernet switching fabric. Sure, VMware supports virtual vlans for each individual host, but it would still be visible to the hosting company. Http/port 4444 traffic would be visible, but https/port 4445 would be encrypted by SSL.

However, if you're running openvpn on your own installation on the vps, then it would be encrypted and only visible in the memory on the vps.

There's a good forum for i2p on reddit, I would ask the experts there as well.

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The solution is to setup proxy (I use tinyproxy) on VPS and configure it to allow connections from VPN. Now it is possible just to switch on VPN and start using proxy.

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