One fundamental flaw I see with this idea is that if you are addressing the method in which I gathered these IPs (via DM), you would have to send decrypted URLs from a users end-to-end encrypted DMs to the image proxy, which endangers privacy in a new way because it revealed part of the message to the proxy. Now you have to trust the proxy with potential secrets.

Link Previews are also a vector for attack here, and it would be even worse to send all DM'd URLs through the proxy.

I also worry that image proxies could bloat the cost of running a client, are a form of centralization (this solution only benefits Damus users), and are a vector for DDoS/Abuse.

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