We desperately want to support it for filter.nostr.wine but we really want it in a header. Seems like such a waste to open the websocket connection when we ONLY want authenticated users to connect.

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Interesting, that would be a good addition, but I could see use cases where clients would want to re-AUTH against clients many times in a single session

Yes, I would propose it as an additional option. Could be the same signed event in a jwt without the challenge string or something for a header.

I don’t see why the NIP couldn’t support both!