Mail is using wrong outgoing server and From address for replies

Question

Level 1

9 points

Mail is using wrong outgoing server and From address for replies

I have two acocunts in Mail. One personal (a gmail acocunt), one work (email thru my web host, call it MyHost.com). Used to be, if I replied from a mail sent to my gmail address, the outgoing reply was sent thru gmail's server. Replies to mail sent to me thru MyHost.com went out through the MyHost.com server. Now, no matter what, Mail replies with the gmail address as the sender and the gmail address in the From slot, and it tries to go through gmail's outgoing email sever. This problem started this morning, and has never happened before.

I have changed nothing, and my settings are correct:

In Mail > Preferences > Account Information, the incoming and outgoing servers and addresses are correct for each account. The gmail account has gmail's info, the MyHost.com acocunt has its MyHost.com info. None of this has been modified for several years, and it didn't change a month ago when I upgraded to Mt. Lion. It's still all correct.

In Mail > Preferences > General, the setting for "If outgoing server is unavailable" is (as always) set to "Automatically try sending later" (not "Show a list of alternate servers").

In Mail > Preferences > Composing, "Send new messages from" is set to "Account of selected mailbox"

I have set no rules regarding these things (not sure you even could).

It all worked fine yesterday. Nothing has changed at my end in the last 24 hours.

Is there ANOTHER setting I should be looking for? Is there a preferences/plist file to delete to restore correct behavior of outgoing mail? As it is now, I have to manually select the outgoing server whenever sending from my work account, or replying to an email sent to my work account. This works (sconfirming that my server settings are correct) but it is a huge pain, and I've already forgotten to do it a couple of times, which looks bad.

Mac mini, OS X Mountain Lion (10.8.2), Mail 6.2 (1499)

Posted on Jan 4, 2013 11:02 AM

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Answer 1

DPBest

Level 1

4 points

Feb 8, 2013 11:11 PM in response to artboygrafix

I'm having the same problem. Mail 6.2 does not properly pick up which account the originall meassage was sent to when doing a reply. I did not have this problem with 6.1. I have six mail accounts and this is beoming a PITA. Apple, are you listening?

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Answer 2

SallyT.

Level 1

14 points

Dec 19, 2013 4:13 AM in response to artboygrafix

I've just started using a Mac and have set up three accounts in Mail. One is Gmail and I am having exactly the same problem. Really annoying.

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Answer 3

artboygrafix Author

Level 1

9 points

Dec 19, 2013 4:46 AM in response to SallyT.

SallyT, my problem went away as mysteriously as it began. I can't really help figure out why it was doing that for a while, but I do recommend this:

1. In Mail --> Preferences --> Accounts tab ...make sure that the checkbox for "Use only this server" is checked ON in the Outgoing Mail Server area.

2. Update Mail to the current version, if you haven't already.

As I said, my settings were correct all along, and it just happened out of the blue. A few days later, it stopped happening just as suddenly. Since then, I've updated to 10.9 Mavericks and the new version of Mail, and the problem has not recurred.

If the above suggestions aren't helping, this last resort might:

Make SURE your Mail account settings are correct.

Quit Mail and all other apps.

Go to DiskUtility in Applications --> Utilities, select your computer's hard drive, and run Repair Permissions. May take a few minutes if you have a ton of stuff on your comp.

Restart your Mac.

Launch Mail, verify each account still has the correct Outgoing Mail Server settings, and test it out.

Hope that helps...maybe you just have to wait a couple days more, as I did, for the gremlins to die off.

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Answer 4

angelkay

Level 1

5 points

Feb 12, 2014 9:28 AM in response to artboygrafix

I've had the same type of problem--sending an email from one account, but the replies coming back to another email account. Here are the 3 possible steps to fix the problem.

1) Go to Mail-->Preferences-->General and set "If outgoing server is unavailable" to "Automatically try sending later"

2) Mail-->Preferences-->Accounts--Account Information, for each account check the box the says "Use only this server"

3) Mail-->Preferences-->Accounts-->Account Information, look for the drop list at the bottom labelled "Outgoing Mail Server (SMTP)". Click on the droplist and select the bottom item, "Edit SMTP Server List". Click on the Advanced tab. Check if your Authentication is set to "Password." Then make sure that the bottom Password box is filled in. (This is what was missing on the email accounts I started having trouble with. I don't know how they had disappeared, as it had been filled in before, but the missing passwords were my problem.) You need to do this for every email account to make sure the authentications are correct. You will be asked to save each change.

When finished, close out of Mail and restart.

I hope this helps!

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Answer 5

LostLake

Level 1

0 points

Mar 13, 2014 9:33 AM in response to artboygrafix

In case you anyone else comes looking for this issue:

Mail-->Preferences-->Composing--> Under Addressing, Send new messages from, select account of selected mailbox from dropdown menu...

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Answer 6

Aug 17, 2015 1:00 PM in response to LostLake

I called Apple about this issue before I found your posting. They were giving out incorrect information about the issue at the SUPERVISOR level! Thanks to you, there was a quick, easy fix. You trained the supervisor!

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