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I think so.
I have "When you receive a new comment in a private message" ticked.
If i start a conversation by sending a new message, when i get a response, i do not get an email notification.
If someone else starts a conversation with me, i get an email when they first send it and then for every subsequent reply they send.
Does that make sense?
I'm confused by this, though it sounds like a bug exists I'm not sure I understand it.
Alice and Bob example...
Alice creates a conversation, auto-follows it and sees the "email notification" box checked.
Bob replies to conversation.
Alice doesn't receive a notification.
Is that the scenario?