Mail - Reply from the same address the message was sent to

I recently switched from using Gmail's web interface to Apple Mail. I maintain multiple email addresses, and have been having one particular issue with Mail that was easy to solve in Gmail. I have a university email address, say name@uni.edu. My university's department also gives me the email address name@dept.uni.edu. Unfortunately, the department-specific email address only has POP access available. I do not like using POP since emails read on my phone cannot be marked as read on my computer. When I used Gmail, I simply forwarded the dept.uni.edu email address to the main uni.edu address. I set up a "Send mail as" address in Gmail so that I could send mail from the dept.uni.edu address. I then checked the "Reply from the same address the message was sent to" box, and everything worked like I wanted. Mail sent to name@dept.uni.edu was forwarded to the uni.edu address (which has IMAP support), and if I tried to reply, Gmail was intelligent enough to automatically reply from the dept.uni.edu address when appropriate.


I have found Apple Mail, however, completely counterintuitive. There seems to be no way of doing this, that I can tell, without manually specifying the outgoing account. I currently have set up two separate accounts for the aforementioned email addresses, and switch the "From" address as needed. Is there a solution to this? It's somewhat disappointing that Gmail's web interface is so much more intuitive than Mail, as this is by no means the only problem I have encountered (just the only one I cannot find a solution to elsewhere). This is all using Mail 6.1 on OS X 10.8.2.

Mail-OTHER, OS X Mountain Lion (10.8.2)

Posted on Oct 1, 2012 6:23 PM

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7 replies

Oct 4, 2012 10:54 PM in response to knmorgan

knmorgan,


I am not using 10.8.x and I've read that Mail's behaviour in this regard has changed since 10.7. Having said that I'm curious for you to try this solution:


1. Open Mail's preferences (Please excuse me if I get the screen details wrong. I'm basing this on the 10.7 screens)

2. Go to "Accounts"

3. You only need the ONE account here for your gmail account (you don't need one for the other address)

4. Select that gmail account and select "Account Information"

5. In the "Email Address" field add all the "From" addresses you need, separated by a comma (ie name@uni.edu, name@dept.uni.com). Put the "default" address first (ie The one to use when creating a brand new email that is not a "reply")


Under 10.7 this setup mirrors the same behaviour that gmail has when you've selected "Reply from the same address the message was sent to".


However, as I said above, there has been some comments in the blogs that this behaviour has changed. I'm not entirely sure they are describing exactly the same thing. That's why I thought it might be worth trying.


I'm really hoping that fixes your problem. I've been holding off upgrading to 10.8 because I can't afford to lose this feature.


GOOD LUCK!

Oct 5, 2012 8:47 PM in response to Scotteth

It automatically selects the correct "From" address in the drop-down menu. To be specific, I have one account active in Mail: name@uni.edu. I set up name@dept.uni.edu to forward to name@uni.edu, and entered both (separated by a comma) in the "Email address" field in account preferences. Now, both email addresses are retrieved by my uni.edu account, and Mail replies from the correct one. Hopefully this helps.

Feb 15, 2013 3:40 PM in response to knmorgan

In 10.6 & and 10.7 versions of Mail, when you hit "reply," it automatically chose the correct From: address, based on the To: field of the message you were replying to.


In 10.8, *for messages that have been processed by rules* (i.e. filtered automatically into local folders) this functionality is apparently broken. Looks like a BUG in the Mail.app v.6.2


See these very informative, exhaustive discussions:


https://discussions.apple.com/thread/4148125

https://discussions.apple.com/thread/4273912

Jan 17, 2013 1:48 PM in response to Scotteth

This almost works, but it does not use the live.com SMTP servers like it does from Gmail.com web interface. It uses the Google SMTP. Basically it seems to be sending with "on behalf" type of situation vs. from live.com like I want (and used to be able to do automatically with older versions of Mail.app). This causes deliverability concerns for me.


Any other ideas for a work-around?


Thanks.

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Mail - Reply from the same address the message was sent to

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