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In OS X Mail, when I enter the name of a person to whom I have sent a previous e-mail, I'm often presented with a suggested e-mail address, corresponding (roughly) to the most recent frequently sent-to person matching the entered name, or part of a name. These suggestions make sense, and I realize that they are coming from my previous recipients list, but what I don't understand is this: often, though the proposed address is associated with a contact in my address book (and is marked as such in the Previous Recipients list), it is not recognized as being associated with the contact in the sent message. For example, if I have a contact, say:

Joe Stack
joe@aaa.com
joe@bbb.com
joe@ccc.com

and I have been corresponding a lot recently with him at joe@bbb.com then when I begin typing his name in the To field rather than proposing

Joe Stack

along with context menu containing a list of all of the e-mail addresses from his contact information, I get

Joe Stack <joe@bbb.com>

with no alternate choices of e-mail and no connection to his contact. In fact, in the context menu for this address, I'm given the option to Add To Address Book rather than Show Contact Card (and if I add it, it is added as a distinct additional entry, so that now there are two entries with joe@bbb.com as an e-mail address).

What could be causing Mail to fail to recognize that the joe@bbb.com address is for an existing contact? This behavior has been going on for some time (at least since 10.6) and continues in Mountain Lion.

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Note that this behavior is not Lion (or if I recall correctly, even Snow Leopard) specific, but has been present for some time. –  raxacoricofallapatorius Nov 12 '11 at 22:53
    
What happens if you add to address book? Is it just this one contact? –  Robin Feb 15 '12 at 22:16
    
@Robin: The (very many) e-mail addresses in question are already in the address book. The issue is that Mail behaves (often, but not always) as if they're not, once they're also in the Previous Recipients list. –  raxacoricofallapatorius Feb 18 '12 at 15:57
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3 Answers

up vote 1 down vote accepted
+50

Honestly, I believe that this is a bug in mail.app.

I think that if you report it to https://bugreport.apple.com, they'll give you some scripts to run, and will ask you to send some special logs.

I know this isn't a "solution", but maybe it will help improve the app for all of us..

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It is indeed a known bug: 6056296. –  raxacoricofallapatorius Aug 15 '12 at 0:47
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I was having the same issue. To resolve it, I went into the previous recipients list and removed all entries of the offending address, as well as any other email addresses associated with that person. From that point forward, when composing an email it correctly pulled the Address Book entry and not the independent address.

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Yes, but that's not the question. And are you saying doing this once fixes the problem forever? That's not been my experience. –  raxacoricofallapatorius Feb 15 '12 at 16:30
    
I'd appreciate it if someone could confirm that this actually works for them: specifically that it continues to work once the address reappears in the recents list. –  raxacoricofallapatorius Aug 14 '12 at 0:09
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This could be due to entries in your previous recipients list. This list is accessed in Mail via the Window > Previous Recipients menu item.

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Yes, as I mention in the question, I'm aware of that. The question is why Mail (sometimes) fails to recognize that those entries correspond to contacts in my Adderess Book. –  raxacoricofallapatorius Dec 11 '11 at 14:19
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