In the case of #1, the recipient npub is not obfuscated. Hence the relay is responsible for not leaking that event outside of the intended recipient.
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Gotcha. But that can already be done with NIP-04. How does NIP-44 improve on that? Just better encryption that does not increase the chance of nsec leakage?
> Just better encryption that does not increase the chance of nsec leakage?
Correct. NIP-44 is not a new DM NIP (that will be another number). NIP-44 just defines a better encryption scheme that any other NIP (including a DM NIP) can use. The offered protections by NIP-44 are against the needs of that individual encryption and not against the needs of a new DM system :)
In other words, you can definitely use NIP-44 in a way that is not private at all. The encrypted parts will be private, but all the other markers in the event can give everything away. It's like citing somebody in a NIP-04 message and adding a p-tag to that person outside the encrypted component.