If the incognito icon lights up, you both are good.

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Discussion

Will I be able to know before I send the first message?

Yep, the incognito will light up if the receiver's DM relay list can be found.

In theory, all NIP-17 implementers must use it. At least 0xchat, amethyst, coracle, gossip, coop use them.

And in practice?

🍿

No idea. I think they use their own relays when the DM relay is not set, without setting the DM list for the user. Which is bad, imo.