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I want a smart mailbox that will display all the emails sent to me by a particular person as well as all the emails I've sent them.

I assumed that setting the rules to be

Contains messages that match ANY of the following;
From Is Equal To Person
Any Recipient Is Equal To Person

but all I get is messages from Person.

This doesn't do the trick so what am I missing? Shouldn't it return any emails sent from Person and any emails wherein Person is a recipient?

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Did you check the box for Include messages from Sent and/or have you moved your sent messages out of the Sent folder into other folders? – tubedogg Aug 27 '13 at 1:30
Yes I have include sent messages set, but it doesn't seem to do anything. I haven't moved anything out of my sent folder. – Tomulent Aug 27 '13 at 1:34
Let's narrow down - remove the "From is equal to" line. Do you get anything then? What if you change Any Recipient Is Equal To to Any Recipient Contains? If that still doesn't work try changing Any Recipient Contains to Entire Message Contains. – tubedogg Aug 27 '13 at 1:36
Changing it to From contains and Any Recipient Contains worked. Thank you! I wonder why that is. – Tomulent Aug 27 '13 at 1:44
up vote 2 down vote accepted

For both rules, change this portion:

Is Equal To

to this:


Utilizing Is Equal To requires an exact match against whatever you trying to match. Depending on how Mail is looking at a recipient's address, it may include brackets around it and/or include the person's name, in addition to the actual email address. These strings wouldn't match just the email address, obviously. Using Contains instead allows it to match the string you know should be there - the email address - no matter what Mail is actually matching against.

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Thanks tubedog! – Tomulent Aug 27 '13 at 1:48

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