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I have two accounts set up in Apple Mail. The second account is for backup purposes and because at times the primary account is unavailable. When that happens, I send from the second account but would like the reply-to address to be that of the primary account. Is there a way to set things up this way in Apple Mail?

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With a message composition window open in Apple Mail make the following menu selection:

View > Reply-To Address Field

That works for a message-by-message basis. If you want to apply all the time there's a hack you can do this via Terminal:

defaults write UserHeaders '{"Reply-To" = "reply-to@address"; }'

More details can be found here.

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If you go to settings, then mail then account, under IMAP information it says Email, click on the arrow on right, then choose add account and enter the email address of the account you want reply sent from and hit RETURNABLE it will add the account then you must click on that account to select it. Hit done and you will be all set.

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Just configure both email accounts with the same email address, but different server details and credentials.

You can set the e-mail address in Preferences > Accounts for each account individually.

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Not all mail servers accept mails with a From: address not in their own domain. – patrix Aug 16 '12 at 19:34
Possible, but I never encountered an SMTP server with such a restriction. – Gerry Aug 16 '12 at 20:19
It's used to prevent spam – patrix Aug 16 '12 at 20:37

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