One issue would be DMs, I haven't tested delegation with them and that would be potentially confusing if it's not handled well by the client.

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I don't think handling dms would be much different than handling kind 1

you don't have root privkey to generate shared secret, it would have to be based on the delegate key. which means logging in with your root key you wouldn't be able to see any of the dms.

you are correct, hadn't thought about that

probably shouldn't enable DMs when using delegation until we figure out how to make that work seamlessly