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I'd like to know how to send a message to a specific member in my organization from within Trello.

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+1 Good question. I don't think it's possible though. You can comment on the back of any card by clicking on it, however anyone can see that. – Web_Designer Jan 19 '12 at 0:31
If you look at trello's public board, you can see a similar idea that people have proposed. – Web_Designer Jan 19 '12 at 0:40
Thanks @RogerAttrill! – Itamar Mar 7 '13 at 18:54

Trello does not currently support direct messages.

We are considering a member-to-member chat feature.

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It should not be just a chat feature since not everyone is online at the same time. But just a general message you can send to other team members to their inbox. – user48597 Sep 30 '13 at 14:44

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