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Re:HashiCorp Boundary by jlgaddis on Thursday October 15, 2020 @11:17AM (#24789467)
It seems like using WireGuard on the "end target" to automatically connect to (WireGuard on) the proxy would be an easy workaround.

I did basically the same thing years ago for remote console devices deployed inside various customer networks where I had little or no control over the network. At that time, I used OpenVPN to automatically connect back to our "VPN servers" -- providing access to the device even if it was behind two or three layers of NAT (which, unfortunately, wasn't uncommon!).

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