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What if the initial connection to the VPN server was established over a hidden service? Wouldn't this be a more elegant and secure solution to VPN over TOR?

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Shortly, no it would not. Hidden services are designed to hide the destination server from the connecting visitor, and it means that

the connection looks as follows: You>Guard>Middle>Exit<->Exit<Middle<Guard<Hidden Service.

Instead of 3 hops which is already a big overhead in terms of speed, latency and CPU, you will get 6. Now 6 doesn't only mean

twice as bad, it means lots more when you effectively measure it. Latency of 2000-3000ms should be expected as normal one.

So this will not be a good idea, and will not be an advantage for any use case.

Occasional moderator, sometimes BOFH. Opinions are my own, except when my wife disagrees.

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