Is there a technical reason why we can't use a waiting room to loosen the association of IP addresses and npubs? Like, the IP address gets stripped once it arrives at the relay into the waiting room, and the relay processes the events thereafter? Or is that really stupid??

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The problem is that the client doesn't trust the relay. If you are the relay, and you are an evil relay, you probably aren't going to be stripping off any IP addresses. We need a solution that proves to a client that they aren't exposing their IP address to a relay. But of course the way to do this is to use a VPN or tor. If tor is totally unusable than we need to make a new tor. That sounds like a huge project, so I'll bow out and leave it to the rest of you.