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I have 10 email addresses (ranging from POP, IMAP, and Exchange) setup in my Mail.app. There are 2 addresses I use primarily. But only one can be labeled Default. Therefore, when "inbox" is selected, and a new email is created, it is automatically sending from Default.

Is there ANY way to set Mail.app to ask me which email address I want to send from if it is a newly created email (and not a reply to an email I've received, in reply situations I have no issue)?

Once I hit send, it should then ask me from what address to send from.

  • Mac? iOS? What are we talking about – Rob Mar 9 '14 at 19:29
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    @Robuust The question is tagged with OS X Mail, so I presume Mac. – grg Mar 9 '14 at 19:49
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The easiest way (at least the one I know of) is simply selecting the mailbox on the left you want to send from, and then click the new mail icon. It will put as send-address the mailbox you selected on the left.

You can always use the dropdown afterwards if you want it to be another address, but that's the easiest way. To make it more convenient, set the boxes as top 2 and you can easily select one of both.

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