Mail.app mailbox selecting incorrect outgoing server

I have never run into this issue before and I am racking my brain trying to figure out how to fix it.
As of yesterday, my primary email account is using a secondary outgoing email server by default. The only way to prevent this is to manually select the primary email account after I open the email.
For example:
My mailboxes look like this (four accounts, all iMAP):
One
Two
Three
Four
When I select "One", the new email window opens as if I have selected mailbox "Two". It's defualting to "Two". If I delete "Two's" outgoing smtp information, "One" will open as itself. If I open "Three" or "Four", they open as their own default mailboxes.
In Mail preferences > composing, I have it selected to "Open as selected account". When I change it to "Open as 'One'", then mailbox "One" will open as "One". When I change it back to "Open as selected account" it goes back to opening mailbox "One" as mailbox "Two".
All of my Account Settings in preferences are set up identically. They are 4 different iMap accounts using mail.smtp.com as their outgoing server with their own SSL and username/password authentication.
I have googled the issue in every way I can think to word it and have found similar issues, but none of the fixes for those seem to solve my problem. Any help would be greatly appreciated.

I have this same problem - and it is a big problem! Why can't I select the right mailbox for my email to come from any more either? Is someone from Apple looking at this?

Similar Messages

Mail does not use correct outgoing server

Problem
Mail in Mavericks (and also IOS6 snf 7) does not use the outgoing smtp server associated with the account being used. This results in either a failure to send or mail being put into the wrong "Sent" folder.
Background
I have most of my non-icloud mail pulled down to a home server from which my laptops and ios devices access various accounts using imap. The local home server also provides smtp and relays all mail to my ISP. Recently I have been switching from an old home server (Mac Mini) to a new one (Raspberry pi running the debian Raspbian version with fetchmail, Dovecot and postfix setup).
While making the changeover I had access to both the old server and the new server enabled on my laptop. Naturally the majority of the settings (Name, email address etc) were the same although the name and address of the server to be used for both incoming and outgoing mail were different. This seemed tp work fine for incoming. However when I tested outgoing mail the copy that should appear in the "sentt" box went missing. This usually indicates some mistake in the setting of the sent mail folder on the accounts but this all checked out.
I eventually found the missing outgoing mail intended to go through the new server in the sent box on the old server. Further trials showed that no matter what I did the outgoing would always default to the old (and therefore first set up) outgoing server.
Deleting the old account and the old outgoing server of course should cure the problem and will eventually be the solution for me when I kill the old server. But i wanted to get to the bottom of the problem in case it reappeared in other contexts. Checking the "use only this server" box produced failure to send rather than the correct result.
Trialing various alterntaive settings showed that the problem occurs when there are two outgoing servers with the email address in the settings and the user name on the outgoing server name being the same. I had assumed that changing the description field would distinguish between the various settings; however this did not work. Changing the Name Field did work eg by putting (O) after my name.
It appears therefore that mail selects the outgoing server on the basis of email address (with the full name included) and user name (trrespective of the actual server or the Description that shows in the smtp server listing. In some ways this is logical but it produces problems in the context I have described and would also be a difficulty if you wanted to use an alternative server when in a different location.
I have trawled support and elsewhere for any thing similar. Lots of mail problems (don't get me started on the way icloud loses outgoing each time you edit the list!) but I have not found any posts on precisiely this point.
IOS devices seem to have similar problems, but a quick attempt at a similar solution does not work, and I cannot be bothered to test the options. I will simply clean them out and put in the new accounts.
Advice
Grateful for any comments or advice from people who have encountered similar problems and whether my diagnosis if correct. Have I missed any obvious corrections that would clear this up. I do not know whether this is a Mavericks issue or also appears in earlier OSX versions.
CPE

Peter,
Where ever the Sent and Trash folders show in the Sidebar, highlight first one, and then the other, followed by clicking on Mailbox in the Menubar, and choosing Use This Mailbox For, and choose the function.
Keep us posted on your progress.
Ernie

TS1702 cannot send Mail   The connection to the outgoing server failed. Additional Outgoing Mail Servers can be configured in Settings Mail, COntacts, Calendars

Cannot send outgoing messages from my IPhone. Receive the following message:
               Cannot Send Mail
               The connection to the outgoing server"[email protected]" failed. Additional OUtgoign Mail Servers can be configured in Settings> Mail, Contacts,                Calendar

See here for troubleshooting the SMTP settings (outgoing mail server on your carrier's servers)
http://www.apple.com/uk/support/iphone/mail/
Often removing a mail service from iPhone and resetting works

IPhone message. "Cannot Send Mail" "The connection to the outgoing server.

It states:
"Cannot Send Mail" "The connection to the outgoing server "(null)" failed."
This is the error I get attempting to send Yahoo mail using EDGE network on at&t.
I would guess that only 2-3 emails out of every 10 go through. The rest get the above error message.
Please help if you can.
Thanks

Well, if your on ATT Yahoo. The settings are as follows, and I've had luck both sending and recieving with these settings.
Incoming Mail Server
Host Name: pop.att.yahoo.com
User Name: *****@sbcglobal.net (or whatever your ATT domain might be)
Password: Required
Outgoing Mail Server
Host Name: smtp.att.yahoo.com
User Name: ****@sbcglobal.net (or whatever your domain happens to be)
Password: Optional (I left mine blank)
Under Advanced
Deleted Messages: Remove After ? (Your Choice)
Incoming Settings
Use SSL : On
Authentication: Password
Delete from Server: Your choice
Server Port: 995
Outgoing Settings
Use SSL: On
Authentication: Password
Server Port: 465
I've taken these setting from my phone. I can't remember all the domain names for the ATT Yahoo, but I know sbcglobal is one, and I believe attglobal is another. Also to change the ports under advanced, though you shouldn't have to, simply click the port area and a keypad will come up below. You can type the port number there.

TS1398 My iPad cannot send mail - the connection to the outgoing server failed

My iPad cannot send mail - the connection to the outgoing server failed.

Go to the email settings, and re-enter your Outgoing Server username and password.
Have you changed that recently, perhaps on the Incoming Server but not on the Outgoing server?

Mail.app supports accessing to Exchange Server through WebDAV OWA

I have been reading many threads from both here and Microsoft in order to get my mail.app work with my Exchange Server via WebDAV and/ or OWA.
My case is that I am fine with Entourage but not mail.app.
Something a few of us may miss is that Mail.app automatically amend the field "Outlook Web Access Server" to something like mail.myserver.com regardless of what you type, as in most cases the correct address is mail.myserver.com/exchange
So I am digging into my ~/Library/Application Support/Mail and try to find where exactly mail.app store the Account Information but I came out with no luck.
Can someone guide me through where is the setting stored because I think forcefully change that "auto change" Outlook Web Access Server address may well fix the problem many of us face.

With 10.5 and Mail 3.0, any luck for this topic?

Mail selecting incorrect SMTP server

I saw a post on this but I have a more specific problem, hopefully someone can tell me what I'm doing wrong. Here's my situation. I use my MacBook Pro at work, and I have to operate sometimes inside a firewall and sometimes out on the Internet. As a result, I have to maintain two different Account setups in Mail for the same actual email account. One setup (call it 'Mail') goes directly to the server address, uses normal SSL transport, and uses that internet SMTP server with SSL authentication. All works fine. However, when I'm inside the firewall, I have to use an SSH tunnelling setup to get to IMAP servers outside, so I use SSHAgent and tunnel my local ports to the server outside. That, also, works after much fiddling.
So I end up having two different 'accounts' in Mail - one to 'Mail' and one to 'Mail Tunnel.' At any given time, one or the other works, and the other is 'offline.' Here comes the problem.
I have specified in each of them that they have to use specific SMTP servers - the direct connection for 'Mail' and the localhost:port for 'Mail Tunnel.' The problem is that whenever I compose and send a message while inside, Mail.app always tries to send it to the 'Mail' SMTP server - the one with the direct address. Even if I'm sitting in the 'Mail Tunnel' inbox when I hit 'compose' - no joy. It always tries the 'external' mail server.
The only way I can send mail while inside is to go into preferences, go to the 'Mail' setup (not Mail Tunnel) and set it to use the localhost:port SMTP server and select 'Use Only This Server.' Then things work, until of course I leave the firewalled zone and have to go back and change preferences.
So what appears to be happening is that Mail isn't differentiating my outbound mail server based on the account I'm using. I'm wondering if that's because my 'REply-To' address and username are the same on both accounts, so somehow the SMTP server selection doesn't get done? I know there's a preference in the 'Composing' section to set where to send mail from...however, the only options there are '<my email address>@<my domain>' or 'Account of Last Viewed Mailbox.' I have it set to the latter. It doesn't say anything about what server to use, and the face that it's keying on my email address (which is the same for both accounts) leads me to believe that's what's going wrong - since the email address is the same in both cases, Mail.app doesn't think it has to select the outbound server. In other words, it's indexing on my Reply-To address, not on the 'Account profile.'
Am I crazy? Is there a way to make this work? Thanks.

And, if you select Mail's Accounts preferences in the Accounts Information tab, then select the Edit servers option from the drop down menu for Outgoing server, is each server associated only with it's respective account? And when observing the Outgoing server drop down menu does the name of the associated server change when you select each account from the sidebar?
If none of this is working still, then you may want to remove the /Home/Library/Preferences/com.apple.mail.plist file to the Desktop. Then reconfigure Mail's preferences to see if that resolves the problem. As it is I cannot replicate what you've described on my system, so it could be a corrupted preference file on yours. You can test this by creating a new user account and logging into that account. Set up new Mail configurations for the new account to see if they function as expected.

Corrupted attachments in Mail.app connecting to an IMAP server

Hi,
I'm using Mail.app to connect to our local IMAP server (over SSL). For a long while, I've had problems with large attachments being corrupted when I open a message in Mail. If I view the same message in our webmail client (which also talks to the IMAP server), the attachments are uncorrupted.
If I save a message as source and decode using a mime64 decoding tool, the attachments are corrupted in the same way as from within mail. This is most clearly visible when the attachment is a large jpeg.
If I remove the locally cached messages by deleting the /Library/Mail/IMAP-xxxxx folder, then re-download all the messages, the attachments will be often corrupted in a different position in the image.
Using another IMAP mail client (Thunderbird) on the same machine to connect to the same IMAP server shows no corruption in the same messages which are corrupted in Mail.app.
I can't say whether this problem was introduced with Tiger, but it has persisted for a long time. This problem is only for INCOMING attachments; I have had no problems with corruption in the attachments I send to others.
Other Tiger Mail.app users in the building have the same issue. Any suggestions to identify and fix this problem will be greatly appreciated. It's possible it's bug in Mail, and I would be happy to contribute any information or perform any testing required to fix it.
Using:
Mail.app v2.1 (752/752.2)
Thunderbird v1.5.0.7 (20060909)
Mac OS X 10.4.8 Build 8L127
1 Ghz Powerbook G4 with 1.25 GB RAM
Best regards,
Dylan
Powerbook G4 Mac OS X (10.4.8)
Powerbook G4 Mac OS X (10.4.8)

The right way of doing that would be rebuilding the
mailbox, i.e. select it and do Mailbox >
Rebuild. Does that make a difference?
Rebuilding the mailbox — no difference. The attachments are corrupted at a different position in the image, but still corrupted.
Another thing to try would be trashing the Mail
cache, i.e., quit Mail, in the Finder go to
Trashing the Mail Cache — no difference. The attachments are not re-downloaded from the server, and so the position of the corruption in the image doesn't change.
What happens if you move or copy the message to a
local "On My Mac" mailbox, and open the local copy
instead?
The local copy then has corrupted attachments.
/Library/StartupItems/
Empty.
/Library/InputManagers/
SIMBL
~/Library/InputManagers/
Empty.
/Library/Mail/Bundles/
Empty.
~/Library/Mail/Bundles/
GPGMail
Mail.appetizer
A quick test — disabling these plug-in components has no effect on the corrupted messages, even after re-building the mailbox in question.
I should point out again that it's not just my machine that's affected by this problem. I verified today that other users of the same server are also affected. This isn't likely to be caused by a quirky configuration on my machine.
Also, open System Preferences, and go to
Accounts > Login Items. What do you see
there?
LittleSnitchDaemon
iCalAlarmScheduler
iCal
Mail
SmartReporter
LiteSwitchX
MicrosoftMouseHelper
MouseLocatorAgent
Skype
Last.fm
Renicer
The items below the line have been added recently, and the problem was definitely there before hand.
Dylan.
Powerbook G4 Mac OS X (10.4.8)

Mail App deleting messages from .Mac server

Hi
I haven't seen this issue on this board. Let me know if I'm wrong.
This is on the interaction between my .Mac email account and the Mail Application. I have two email accounts set up.
I have 2 computers and keep my mail on one, so I kept my previous (Eudora) mail apps set to "leave mail on server" on the other.
I don't see a setting for this for my .Mac email account in Mail.app. When I check my mail with the Mail.app recently, on the computer where I don't keep my mail, it is deleting the mail from the .Mac account. I don't think it did this before. The mail is no longer on .Mac when I check via a browser.
My earthlink pop account seems to be working fine.
Any suggestions would be most appreciated
Quicksilver G4 Mac OS X (10.4.6)

Whether it's correct or not depends on the
circumstances under which mail is removed from the
server. If it's because it's being moved out of the
account Inbox and into "On My Mac" custom
mailboxes, then yes, it's correct.
For IMAP-type accounts, mail on account mailboxes are
stored on the server instead of locally (you can
configure this behavior for mailboxes other than
Inbox in Preferences > Accounts > Mailbox
Behaviors). Whatever you do to that mail you're
doing it to the mail stored on the server. If you
tell Mail to move a message out of Inbox,
that's what Mail does, it moves the message out of
Inbox at the server.
Thanks -- so if I understand this properly, the mail is stored on the inbox on the server, but if I have a rule that moves it to a mailbox that I created locally (imported from Eudora, for example) it moves it from the server to my local mailbox *not leaving a copy on the server*. I have lots of mailboxes that I use to sort the mail and rules to route messages. So to correct this issue I should disable the rules if I don't want the mail moved off the server and into a local mailbox.
Many thanks for your help and patience
Quicksilver G4 Mac OS X (10.4.6)

Answering mail: Mail app auto-selects subject

Hi,
today i experienced a very strange behaviour in mail app - this happens with every kind of mail (imap, pop, exchange) :
When I'm answering to any received mail by clicking the "Answer" button/link, the answer mail opened. So far so good. But if try to enter the subject, system auto-selects entered text starting after the second entered character. The count of auto-selected characters depends on my writing velocity. The problem is, that after system auto-selects entered text whilst I'm continuing typing, my text is replaced with the next typed characters. So I'm not able to write any word.
I know it sounds strange, cause it is strange. First I thought there is someone behind me who did this with a kind of remote control. But after a few investigations i found out, that this behaviour only happens, when I'm answering a received mail or if I clicked on a "mailto:" Link in another mail.
I' using a brand new 15'' MPB with OS X Maverick with all latest patches (incl. Mail-Patch).
Is there any new functionallity in mail app which i did not realise???
Greez

Hi,
I found a way to prevent this odd behaviour:
Deactivate spell check while typing. That's it.
I do not know, why spell checking behaves like that, but....
Bye

Mail.app stops synching with Exchange server

It's my second day using Lion at work, and things have been going pretty smooth. That is, except for mail.app. I opened my copy of Exchange on my PC in the office (to set the out-of-office message (if there is one in mail.app I havent found it)) and was surprised to see a bunch of mail waiting for me. I right-clicked on my Inbox in mail.app, chose Synchronize and... nothing. I figured I would close it out and restart it. When I choose Quit, nothing happens. If I go back again Quit is greyed out. There are no apparent dialogue windows or anything open that should stop it. Finally I have to Force Quit the app and restart it. Upon restarting most of the messages appear again in seperate windows as if I hadn't hit sent yet. I close them out and all of my mail is waiting in the Inbox like it should be.
I'm using the Exchange connect feature introducted in Snow Leopard.
This is the requisite "I had no problems with this setup until upgrading to Lion" line.
Is anyone else having this problem? Anyone have a fix?
Thanks!

Is Mail > Preferences > Accounts > Advanced > Automatically synchronize changed mailboxes checked? It shouldn’t...

Delete emails on Mail.app and remain on gmail server

Hello,
I have 128 GB HDD and many emails syncing by Gmail IMAP. Thousands of emails are stored on my HDD and most of them I will never use in the future. Despite this I'd like to keep them in gmail server, just for case...
I was trying to reduce size of my Mail.app for very long time and nothing works correctly.
Ideal situation would be something like this:
E-mails older than 2 months will automatically delete from Mail.app but not from server. Or it doesn't have to be automatic, but I have to keep them on gmail.com. I'm not sure if it is possible with IMAP.
Please, do you have some experience with this problem?
Thanks,
Jan

Hi jvaclavik,
Mail that is kept in an IMAP account will show in your mail account on the Mac but it stays on the server. See this article -
iCloud: IMAP
http://support.apple.com/kb/PH2585
You may want to use the Mac OS X Mail Archive feature, described here -
Mail (Mavericks): Archive messages
http://support.apple.com/kb/PH14894
Gmail has its own Archive feature, described here -
iOS: Understanding Gmail Archive
http://support.apple.com/kb/HT4207
Though the article is in support of iOS devices, the archive feature applies to Macs as well.
Thanks for using Apple Support Communities.
Best,
Brett L

Mail app, mailbox content

Have a dysfunctional Mail as others have mentioned, post-10.4.3 update. Looked for Preferences Mail plist as some have suggested-- was not even in the folder. App does not even open.
Have been using web access to e-mail, and could shift to Netscape, already installed. My wife's question is-- if Mail does not open, is there a way to import the archived messages in the mailboxes from another app? I see where the files are.
PB 867 Mac OS X (10.4.3)

I spent 3 hours on the phone with Apple about this working with a senor tech. It is supposed to work. He seemed to feel that something happened during migration of files (in my case). Nothing I did got it to show.
What he did as a temporary fix is make a file which I called On My Mac, then moved my mailboxes into that so I can open or close it.
I use Gmail. He had me set up a new administrator and it showed Smart Mailboxes but then disappeared.
He is sending this on to techs since it is a problem. I also told him to look around the forums because this is a problem that others are having.
When I get an answer I'll post it here.

Mail unable to connect with outgoing server...

Hi everyone!!
I've been having a problem with mail for the past week and i can receive but cannot send any mail.
Checking the connection doctor there's a message saying it "couldn't connect to the SMTP server" although i have the passwords set correctly on the account prefs.
What seems weird is that last week when i had the same problem, i reset the router and it was fixed, unfortunately it won't work now.
Any ideas please?

I've got exactly the same problem. My mail was working fine a couple of days ago. Now it won;t send mails. Not settings have changed. What could be the cause and how do I sort it? Anyone? Could you mail your reply to [email protected] as I'm about to travel for a while and will only pick up mails on i phone. thanks

Mail app constantly synching with iCloud server after upgrade to Mavericks

Since upgrading to Mavericks, Mail has been constantly synching with the iCloud server - and I mean constantly. I know this because I have the Activity window open. Consequently there is often a significant lag between clicking Send on a new message and it being sent, or new messages being downloaded. I have another iMac at my office and the same problem is being experienced there.
I left the computer running all night to see if it would eventually sych everything, but it seems to be going in a constant cycle ever since the upgrade.
If it means anything to anyone, the Console window displays a continuous stream of data similar to this:
9:24:37.448 am fseventsd[48]: implementation_added_client : failed to add client for path /Users/Kevin/Library/Mail/V2/AosIMAP-kbish…
9:24:37.449 am fseventsd[48]: implementation_register_rpc: implementation_added_client() => 22
9:24:39.808 am fseventsd[48]: implementation_added_client : failed to add client for path /Users/Kevin/Library/Mail/V2/AosIMAP-kbish…
9:24:39.809 am fseventsd[48]: implementation_register_rpc: implementation_added_client() => 22
Can anyone offer any advice on what the problem might be and how I might fix it.
Thanks,
Kevin

No solution here, but I have either the same or a similar problem. Apple Mail with Gmail (IMAP) used to work fine with Mavericks.
Now with Yosemite most emails load ok, but some show the spinning wheel and "Loading..." message forever. These messages never load.
I also have Thunderbird and it loads and shows these messages just fine. The messages that don't load in Mail are simple plain text messages so it's unrelated to complex attachments and such.
Clearly something is broken in Yosemite that wasn't broken in Mavericks.

Mail.app mailbox selecting incorrect outgoing server

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