"Mailing list mode" の「新しい投稿ごとにメールを送信」設定で、自分の投稿に対するメールが送信されない

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Yeah I think that is it, mailing list is only for topics, not for messages.

Can you use a secure category there?

I do not think we have an “echo” mode built for PMs/Group messages, that would be a new feature request.