Mail sent from one account comes back as another

Question

Level 1

95 points

Mail sent from one account comes back as another

Folks:

I recently moved up to 10.9 after many years in 10.6 . . . I have multiple email accounts set up in both [I have a triple boot 09 MBPro] . . . but, lately spending most of my time in 10.9. A number of times I've had Mail highlighted in my top account, sent an email from it . . . but the reply comes back to the number two account, marked as being from the second account?? Checking "sent" from the number one account shows it was sent from that account; but the return/reply comes back to the number two/marked as "from" the second. The two accounts are separate types and it is somewhat embarrassing to have this happen . . . since "accounts" doesn't have any "send as" or "reply to" options I don't know how this is happening . . . . Actually a few years ago my wife's MacBook running 10.6 had this same issue . . . don't think we ever solved that problem . . . so I think it's a "known issue" with Mail . . . just don't know what is "known" about it.

Thanks,

e.e.p.

MBP 15 2.53 GHz, Mac OS X (10.6.8), iBook G4, 14, 933 MHz (10.4.11), iMac G4, 15, 800MHz,

Posted on Jan 13, 2016 6:00 PM

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Answer 1

Eric Root

Level 10

685,317 points

Jan 18, 2016 1:50 PM in response to este.el.paz

Try Mail/Preferences/Accounts /Account Information. Select an account, then go to Outgoing Mail Server (SMTP). From the drop down menu select Edit SMPT server list. Then set up a server for each mail account so that is associated with the e-mail address. Then go to each account and set that server as the Outgoing Mail Server (SMPT). You can click Use only this server if desired.

Mail/Preferences/Composing/Send to messages from - set to account of selected mailbox.

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Answer 2

este.el.paz Author

Level 1

95 points

Jan 14, 2016 1:27 PM in response to Eric Root

@Eric:

Appreciate the reply . . . I'm jammed right now, but, hopefully tomorrow I'll have time to go through and check this out. It should be correct, and I believe I have checked these items before . . . . I did have to change the password in one of the accounts a couple months back . . . but, this seems like an intermittent problem, not entirely reproducible, but irritating when it does happen . . . .

I'll post back when I can check out this data . . . thanks.

e...

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Answer 3

Eric Root

Level 10

685,317 points

Jan 15, 2016 10:22 AM in response to este.el.paz

You are welcome.

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Answer 4

este.el.paz Author

Level 1

95 points

Jan 15, 2016 5:53 PM in response to Eric Root

So, that did show up the problem . . . perhaps this is a case for "connection doctor" . . . the mailbox in question is one of three Gmail accounts that I have in Mail . . . . At one place I work, or maybe both the internet connection is unstable . . . and at one point I recall seeing that the "error" windows were next to all of the accounts . . . they were "offline" . . . and I did the "take all accounts online" gambit . . . . Today, checking Pref/accounts as you suggested the top email account showed "Gmail (offline)" in the Outgoing Mail Server slot . . . not quite realizing that each of the "Gmails" listed belonged to one specific account I selected the next "Gmail" in the drop down menu . . . .

And I sent a test email, went out listed as it was supposed to, but came back in to two of the accounts . . . I believe named as the account it went to?? Anyway took a couple tries to realize the top "Gmail" is the one for that account, I set it to "use this server only" . . . I quit Mail . . . but it still shows as "offline." So, that clearly is the problem . . . the question is the fix . . . perhaps I'll try "connection doctor" and see if that fixes it . . . .

But, again thanks for the hints . . . any further thoughts, let me know . . . I took a couple shots with the iPod if you can't imagine what I've described . . . fairly straightforward . . . even "obvious" if looked at . . . .

[edit: connection doctor shows outgoing fails . . . "check password" . . . I did, it should be correct, I entered it again . . . ????]

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Answer 5

Eric Root

Level 10

685,317 points

Jan 16, 2016 8:54 AM in response to este.el.paz

Delete the password from Keychain Access (Applications/Utilities). While there, Keychain Access menu First Aid.

Keychain Issues - Resolve see post by Kappy

Mail troubleshooting - Yosemite

Mail (Yosemite): If you can’t send messages

Mail not sending or receiving messages after updating OS X

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Answer 6

este.el.paz Author

Level 1

95 points

Jan 16, 2016 4:54 PM in response to Eric Root

@Eric:

Thanks again for the suggestions and the links . . . Kappy is an online friend of mine . . . . It's probably going to be a day or more before I get the time to play with the MBPro and Mail . . . one thing that the Kappy tutorial mentioned was something about needing to be in the root account, and I mostly play in a regular user account, since I live in metro LA a little extra paranoia is "justified." So, might be I need to log into root, and then check the passwords to see if they are the "old" or the "new" and then either try to adjust them or, as you suggest, just delete them . . . .

I'll let you know how that turns out . . . and I'll clean up with the "helpful" or "solved" buttons when I get it done . . . .

e...

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Answer 7

este.el.paz Author

Level 1

95 points

Jan 18, 2016 1:56 PM in response to Eric Root

@Eric:

Yes, deleting the item was what fixed the problem . . . as far as I can tell. Changing the password didn't seem to "work" . . . deleting it, then entering the correct password in the drop down menu when I sent a test email . . . got it done . . . .

Thanks,

e...

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