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Mail.app allows to send emails from multiple mailboxes by enumerating them in comma-delimited format in:

Preferences-Accounts-Account Information-Email Addresses = test@bar.com,test@foo.com

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This feature allows you to seamlessly reply from test@foo.com whenever email was sent to this email by hitting 'Reply' button.

However when test@foo.com receives messages from some mail list list@lists.foo.com, and a message is sent to that list rather then mail address, 'Reply' will pick just a first available mail address, which would be test@bar.com.

Is there a way to specify that replies to list@lists.foo.com should be sent through test@foo.com?

  • Where do you add the information for multiple "from" addresses to (the line starting with Preferences-Accounts-Account)? Don't remember having seen anything like that in Mail.app. – nohillside May 15 '14 at 8:06
  • Maybe it's because I am using Gmail. But I thought it's not specific to email server. – Ty1er May 15 '14 at 17:04
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While replying you can turn on the Reply-To header which will let you set this. You can do that by either going to the View menu and turning on Reply-To or you can do it right from within the message itself, which is easier.

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Alternatively you can try changing the default preferences via the command line. Chances are the Mail defaults won't have a Reply-To header defined, but you can add the key-pair with this:

defaults write com.apple.mail UserHeaders '{"Reply-To" = "theemail@goes.here"; }' 

or

defaults write com.apple.mail UserHeaders '{"Reply-To" = "theemail@goes.here"; "Bcc" = "another@address.here"; }' 

If that doesn't work and you're like me and want to reverse those changes to keep preferences clean, you can edit the .plist file and remove them. The .plist can be found at:

/Users/<username>/Library/Containers/com.apple.mail/Data/Library/Preferences/com.apple.mail

I haven't tested the command line approach, but it should work because I looked this up and used that approach on a work machine once.

Hope this helps!

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