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Until now i have run an opevpn server over Tor as a Hidden Service v2 on port 443 tcp. Am now trying the same with v3 Hidden Service and the connection is timing out. I note that the HSv3 creates a unique private_key besides the hs_ed25519_private and server keys when using a secure port such as port 443 which is not the case when using unsecure ports such as port 80? How do you retain anonymity with unique private_keys unless you use an isolated proxy environment such as Whonix? Does anyone have advice or a guide to setup an openvpn server on a HSv3 over the Tor network on port 443 tcp?

Thanks

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well, basically what you're asking is how to make a per-user private keys for your server, I suggest you to try these two guides :

and speaking about the OpenVPN server itself - just set up a hidden service you need and use a pre-shared TLSKey, that's it! Without a TLSKey it's no way to jack in your server, but if you're using a packet-based setup and not compiling OpenSSL and OpenVPN by hand - you better o set up a per-client keys to avoid the unpatched packages risk: Tor will not allow the unauthorized connections so the potential exploit won't reach your setup. But as for me I'm strongly recommending you to build by hand from source OpenSSL, OpenSSH, OpenVPN and Tor - it will bring you the most security from the package matter

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