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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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Simple!

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 com.apple.mail UserHeaders '{"Reply-To" = "reply-to@address"; }'

More details can be found here.

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    Just a note to point out that the current version of Apple Mail (at least in OS X 10.13.6) now leaves the "Reply-To Address Field" option active between messages if turned on. No need to reactivate it each time. – Justin S Barrett Jun 12 '19 at 15:33
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If the View Reply-To Address option is checked, the Reply-To Address field will be blank in an email draft. It can then be populated as desired.

However if then left unpopulated - or if the View Reply-To Address option is unchecked - on email send it will automatically be set. The email address used will be that of the default account as specified in Preferences.

View Preferences

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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 Mail.app 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. – nohillside 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 – nohillside Aug 16 '12 at 20:37
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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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