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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

As of now, you can't. There are a number of alternatives, though:

  1. Use the Chrome extension Hubbr chat for Trello (Beta)
  2. Use the Chrome extension Trello Chat
  3. Mention that person in a comment and he will see it in his notifications, so that he can reply.

We are using the first extension, but the problem is that you have to use Chrome and install it on every device, for using it.

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