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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?
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Alice creates a conversation, auto-follows it and sees the "email notification" box checked.
This doesn't seem to be happening - its not checking the "email notification" box - despite my notification settings being set to email me "when I receive a new comment in a private message" on my profile.
@danb means that when you receive a message back in a conversation you've started, you don't receive an email, but you do when someone starts the conversation.
Is that something you've consciously left out?