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Problem With Mail

I am having a problem with my mail account. I send emails from one account, and the replies are going to another email address. The two are very similar, only differentiated by one letter, but it is a huge inconvenience. How do i fix this?

MacBook Pro, Mac OS X (10.7.3)

Posted on Apr 2, 2012 4:41 PM

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17 replies

Apr 2, 2012 6:07 PM in response to kobyjd

It appears that the reason messages are going to the other account is because people are recieving them from the opposite address you thing you are sending from. This just could possibly be an error on you part thinking you are sending from one account when you are really sending from the other. Can you verify a message you recieved as wrong and compare it to the message actually sent in the sent folder?


First go to Mail preferences and open the Composing tab. Look at the Send New Message From and see that it is checked to show "From Account of Selected Mailbox".


Next, in a new message window, show the Reply-To Address Field and the Sender Account box. When creating new messages, make sure the from shows the correct address you want to send from and the reply to field is empty.


User uploaded file

Apr 2, 2012 6:58 PM in response to HACKINT0SH

Ive checked the gmail settings and those are fine. The email addresses are different, but they are both my full name as the name of the account. What i mean is one will say John Doe <johndoe@gmail.com> and the other is John Doe <johndoe2@gmail.com>. If you understand what I mean.


I always make sure to select the write mailbox, and make sure when typing the new message to specifically chose the mailbox i want it to be sent from. Emailing back and forth with one person to test it out and see, deleted the thread start a new thread, and it would happen again. I believe the person would receive the email as if it was sent from the other mailbox, though thats not where i tried to send it from.


when i try to do it to myself it does not work. it seems intermittent

Apr 2, 2012 7:43 PM in response to kobyjd

Open Mail preferences. Open the Accounts tab. Select one of the accounts. Edit the outgoing SMTP server for that account. You should have one made for that account with the correct user name & password. If correct, click OK. Check the box to use only that server for that account.


Repeat the process for the other account. It should also have it's own SMTP server with the correct user name and password. Name it differently that the other so you will know which is which. Make sure the correct server is shown in the window with the account highlighted and check the box to use only that server for that account.


Make sure each account has the box checked with the correct outgoing server for the account.


When you send messages, it will use only that server for that account now that you have checked the box. If the server fails, it should give you a message saying the server failed and give you the option to use another.


I suspect the most obvious reason it is happening is that the server failed and selected the other server to send from. It happens often. You may not know it if you don't have that checked. It just goes on to the next server in the list. If it chooses the other server, what happens is gmail's default is to change the address to the sender of the server it used to send the message through.

Example: if i use the gmail server to send an email from a att.net account, the gmail server will change the from address to the gmail address by default setup. The reciever see's the gmail address, not the att.net address.

Apr 2, 2012 8:02 PM in response to Glenn Leblanc

Okay so i got rid of the ones in there, one of them had all the accounts on one so most likely like you said, and i created two new ones, one for one account, one for the other, named them seperate, but they should both say smtp.gmail.com right? After i did that, it now shows the first one with (offline) after it. is that normal? Though i tried sending an email from it and it seemed to work fine go through and be received by the correct mailbox.

Apr 2, 2012 8:13 PM in response to kobyjd

They will both be smtp.gmail.com, but each will have a different user name and password. Name them so that you can distinguish which goes with each account. Make sure you have the correct port settings selected. If one shows offline, try taking it online. If it doesn't go online, then a setting is wrong.

Use the connection doctor in Mail and make sure the connection to each is OK.


When you first send in each, KeyChain should ask to save the password unless it's already there.

Apr 2, 2012 8:23 PM in response to Glenn Leblanc

Okay so the account was not offline, just the outgoing server because of this message

"The servers marked with alert icons are in conflict and cannot be saved. Two servers cannot share the same address and authentication settings. Resolve the conflicts and try again."


One had authentication on from a user name and password, the other did not. the one that has an authentication on shows up as offline, the one with no authentication is online. I can not have them both not on authentication because then i get that message.


What do i do to differentiate them? They have differnet emails, different names, different passwords

Apr 2, 2012 8:47 PM in response to kobyjd

I have 2 yahoo IMAP accounts using the same server with a different discription name using Password authentication, different user names and passwords.

Also have 2 att.net accounts set up.


I don't see why the problem with gmail. Delete one SMTP server. Set up one account with the correct information and make sure you can get that one working. When that one is set up and working, try setting up one for the other user account.

Under SMTP account informaiton, Descritpion should be different from the other. Server Name: smtp.gmail.com

Under SMTP Advanced, use custom port 587, SSL checked, Authentication: Password, User Name: email password for that account, & Password: correct password.


Since both have different user names and passwords, they should be able to be created.

Unless: one is actually treated as an alias. When you log into the gmail site, do you have to log into each account to see them or can you see them from one login?

Apr 2, 2012 8:56 PM in response to Glenn Leblanc

i deleted them all. set up one, sent a test email, once it cleared set up the second one and it didnt give me any problems. I had default port checked instead of custom port 587, maybe for some weird reason that caused the errors before? I dont know but it seems to be working each on their own outgoing server now. So hopefully that prevents all future misdirections of emails.


and no i had to log in seperately for each account, for what its worth.



Thank you so much for the support and assisstance.

Problem With Mail

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