Bug in Mountain Lion Mail Still Sends Replies Using Incorrect Accounts

I originally posted this about a year ago, and the problem still persists in Mail on OS X. So if you have problems sending mail that’s been filtered into folders, this explains why; you’ll need to check each message before sending to make sure it’s using the correct outgoing email address.

I’m on a few email mailing lists, and I’ve noticed that Mail, in OS X 10.8, has been doing something odd. Generally, if you have multiple e-mail accounts, when you reply to a message, your reply uses the same account the message was sent to. But I’ve been finding that Mail does not correctly choose the account if messages are filtered into folders; messages bounce because the selected account is not a member of the mailing lists.

There is a setting in Mail’s Composing preferences where you choose which account to use for new messages, but this shouldn’t affect replies.



The problem only occurs when mail is filtered into folders, which I do for mailing lists. If messages are in one of my inboxes, replies use the correct email address, the one that the message was sent to. But if not, they use the default address which is set in the Composing preferences, as shown above.

So, if you filter emails into folders, and have multiple accounts, you need to check every single e-mail you send as a reply from any of those messages. You can do this by looking at the From popup menu when you’re sending or replying to an e-mail. But this is a very serious annoyance, and I hope this gets fixed.

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11 replies
  1. Howard says:

    The problem in this posting seems to be a bit different than what is described in the Apple support thread that you referenced.

    What I have observed is that if a message is in an Inbox, the reply is from the same account as the Inbox.

    If I have filed the message in a On My Mac folder and reply to that message, the “From” depends upon the preference setting for “Send New Messages From.” If “Send New Messages From” is an account name, the reply uses that account as the From. If “Send New Messages From” is Account of Selected Mailbox, the from is the account at the top of list. Of course, neither is the desired account. In all cases, the from should be the account of the incoming email.

    Reply
    • kirk says:

      I’ve been seeing this both in folders on my Mac, and in smart mailboxes (I never actually go to my inboxes; I have smart mailboxes for them).

      But no matter what, replies should always go from the account the messages were sent to.

      Reply
  2. jeff says:

    I have seen this intermittently for a long time on Snow Leopard as well. When I notice it’s happening it’s always the same, I’ll respond to an email and it will use another email address as the from and I will have to restart Mail to get it to stop.

    Reply
  3. Jason Li says:

    Hey! I saw your post as I had the same problem but then I realized I had messed up my settings on Mail.

    This may help your problem. I hope so: Basically I had to go through my SMTP outgoing servers and to make sure that all of my accounts were sending via the correct SMTP setting. (I had multiple Gmail accounts so they were all labeled “Gmail.”) I dug around in advanced settings/dialogues to make sure the inbox and smtp addresses matched.

    That’s it! :) Maybe it’ll help, maybe it won’t but I figured it couldn’t hurt.

    Reply
  4. Fang says:

    Jason’s solution works quite well for me. It is just that it is hard to find the advanced settings to connect accounts with the right servers. Under account information, click on the drop down of outgoing mail server, then you will find “Edit SMTP server list”. Click on that, then you can see the advanced settings.

    Reply
  5. Howard says:

    Further to Jason’s and Fang’s comments:

    SMTP is unrelated to the problem that Kirk and I related. SMTP determines which mail server sends your message, not which email Apple Mail applies to a reply. Using a different SMTP server will not change the “From” email account in a message.

    Reply
  6. Larry Rosenstein says:

    After doing this a few times, as well as sending work mail using a personal account, I created a “Nobody” account with no outgoing email server and made that the default. When this problem occurs, it won’t be possible to send the message until I choose the right from address.

    Reply
  7. Jonathan Fletcher says:

    I KNEW it wasn’t just me, but I heard no one else talking about it. REALLY annoying! A couple times a day I wil have to create a new email because a listservs bounced my post. ::-(

    Reply
    • David Moon says:

      I’ve been a member of ymug ever since I bought my iMac, but I am still very much in the novice class.
      I recently had my machine up graded to Snow Leopard 10.6.8 and also had a larger internal hard drive installed, all this at a recognised Apple retail store. At the same time I changed my email address from davemoon@talktalk.net to davidmoonmail@davidmoon.plus.com
      I now seem to have a similar problem, I can send emails but often when people say they have sent me a reply I can’t find it.
      Only today I have tried to re-established contact with ymug and was asked to visit my inbox to confirm contact and there is nothing in there.
      As far as I know I have never had anything but the very basic set up for emailing.
      Unfortunately I don’t have the knowledge to sort it out, but I do know what was a very useful tool is now too unreliable to use.
      The frightening thing is that if I buy a new machine the problems may still be there.

      Reply

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