This problem persists if we connect on relays that support Tor?

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Yep. Relays know everything about what you are asking and what they are returning, regardless of how many tors for vpns you use.

Correct me if I'm wrong, but doesn't the use of a proxy provide some anonymity? Sure, relays can see everything associated to an IP, but unless the client does something to identify itself (like signing an event, AUTH, etc...), it's just data in aggregate. Can't associate it to a specific npub.

They still need to see your query and will always know which events to send back. From those things, it's very easy to figure out which key you are using.

Makes sense. Would it be technically possible for a more privacy-focused client to seed queries with a few random requests? For example, add a few random npubs to a follow list query. The client then discards the random data received before serving the followed feed to the user. This might be analogues to padding techniques used in VPN protocols to evade DPI.

Only if we find a way to encode the filter amin some homomorphic encryption... 🤔