Messages stuck in library/mail/outbox

When I try to send an email, hit send, the message disappears. It is not in the sent messages in the Mail window. It is, however, in the outbox folder in the library. If I quit Mail, drag the outbox folder to the trash, and restart, I can send a message normally. If I quit mail and restart, the condition will begin again and persist until I again drag the outbox to the trash, etc.
The condition has existed from the day I first started the computer when new. Macbook Pro, 15 in., mid 2010, 10.6.8
It has become really f'ing annoying.
Thanks for any solutions.
G

Thanks! It turned out that rebuilding the mailbox did it.

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Unsent messages exist in Library Mail Outbox but not when I open Mail

I'm trying to retrieve 200 messages that appear to exist in my Outbox on the desktop (in Library>Mail etc.) but that do not appear when I open Mail. This happened because I force-quit Mail when it choked on 200 messages I dumbly tried to send all at once. Since Mail wouldn't run with them in the Outbox, I quit it and went to the desktop and moved them from Outgoing to other folders, such as Drafts and then another mailbox I created. In each case these messages remain invisible when I reopen Mail, but they appear to exist in the desktop Mail folders as .emlx files. Can anyone help me regain access to them in Mail? Thanks!

Thanks! It turned out that rebuilding the mailbox did it.

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I have an iphone 4S with IOS 6.1.3. I use the Gmail app with no issues to send and receive messages. However, when I attempt to send mail attachments directly from the phone's voice memos or camera roll functions, the messages get stuck in the Mail app outbox. I receive no warning that there is an error when sending these messages, they just never send and I find them sitting in the outbox. I've tried resending from the outbox with no luck.
For camera roll pictures, I've gotten around the problem by composing a message in Gmail and then browse and attach the photos to the e-mail. I don't think there is a similar solution for voice memos. The only options within voice memos is to either directly e-mail or text the memos (but e-mail isn't working). I don't see a way to save the memo and attach them like pictures as I can do in Gmail.
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I've been having similar issues with my iPhone 5 and the latest iOS version. I read somewhere else about an issue with having Exchange and Imap in use with Mail being an issue. I had both, but had my Exchange connection to Gmail off. I was still having the issue.
The solution that worked was to delete my Exchange Gmail account. Now, emails are being sent immediately. If you have Exchange and Imap Gmail accounts on your iPhone, pick one and delete the other. Good luck.

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I had an excellent Apple support agent named Luis who helped out. Re-installed the account partially. Discovered that there is in fact a bug in Yosemite. The mail client in mac will not save the outgoing server address and confusion amongst different mail account happens, added to outbox messages stuck. Hopefully Apple will correct bug in later OS X version. Case number 753401346

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there are 3 random messages stuck in my outbox on the retina mb pro running 10.9.4. they won't sent after all tries including restarting computer. anyone have any ideas? everything else is working as intended in mail. Many thanks for any suggestions!
ptkmac

From the Mail menu bar, select
Window ▹ Connection Doctor
Click the Show Detail button. A drawer opens. Try to send one of the messages and post the text that appears. Anonymize any personal information before posting.

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My wife tried to send a message to several hundred recipients last night and the .Mac mail server choked on it. The problem is that the list of intended recipients is so long that it goes off the bottom of the screen and I can't close the window. We have to force quit Mail to exit it (the red button to close the message window is greyed out) and, even though I deleted the outgoing server Mail is trying to use from the accounts list, it keeps trying to send the message. Does anyone know how I can get rid of this thing?
For a hilarious Exposé screenshot, you can go to files.me.com/holtfam/whts6e
Help. Thanks.
Message was edited by: montreal1

With Mail closed, locate the file in Finder and drag it to the trash.
~/Library/Mail/Mailboxes/Outbox.mbox/Messages/the message
As the outgoing mail server is not located on your Mac, taking that action would not disable the 'sending', more probably compound the problem actually as it can't send.

I've noticed several messages stuck in my outbox.

I've noticed several messages stuck in my outbox. I haven't received any kind of error messages. I have to gmail accounts that this is affecting. Sending from my iPhone works, but not from my macbook pro apple mail client. Ive tried rebooting mail, rebooting the computer, and renewing the DHCP lease to no avail. Anyone have any ideas?

Hi docloco,
Welcome to the Apple Support Communities! I understand that have messages that are not sending from your MacBook Pro. I understand that this is happening to two different gmail accounts. This makes me think that it is not an outgoing username or password issue, but maybe an outgoing mail server issue. I suggest confirming the outgoing server settings with the following article. You can confirm the settings on your computer in Mail > Preferences > Accounts.
Mail Settings Lookup - Apple Support
https://ssl.apple.com/support/mail-settings-lookup/
If the settings are correct and the issue continues, I suggest using the article below to isolate the issue to get it resolved.
OS X Mail: Troubleshooting sending and receiving email messages
http://support.apple.com/kb/ts3276
I hope this helps,
-Joe

I have two messages stuck in my outbox

There are two messages stuck in my outbox. Nothing has changed in my server configuration which I checked. Should I delete them and start again?

Mail uses a mail Receiver and a mail Sender. They are fairly independent. The settings for one can be fine while the settings for the other are a mess.
Mail > Window > Connection Doctor ...
... will give you insight into whether this is a connection (and therefore a configuration) problem.

Mail messages disappear from the Inbox, but are still in ~/Library/Mail

Folks,
I'm encountering a perplexing problem on my parent's eMac; any input would be very much appreciated...here's the story:
Over the weekend, I upgraded my Dad's 1.25GHz eMac G4 to Tiger (it had been running 10.3.9). The upgrade went smoothly, and all seemed well. I applied all the latest Apple Software Updates to get the eMac to 10.4.6, and once again, all seemed well. I performed the usual Disk Utility "permission fixing," as well, and nothing came up that seemed unusual. I did notice that I encountered the "spinning beach ball" a fair amount during routine operations, but I attributed this to the fact that the eMac only has 512MB of RAM (it's going to receive another 512 in a few days), and that I was just being impatient, given that I am accustomed to my own machine, which is a relatively snappy dual 2.5GHz G5 with the full complement of 8GB of RAM. A day or so later, Dad reported that the Mail app was not starting; upon clicking the Mail icon, it simply bounced several times, and then simply stopped bouncing. I looked at the crash logs and found that Mail could not locate a needed file/library located in /System/Library/Frameworks/SyncServices.framework. In addition, I noticed that the iCal app and the Address Book app were also crashing (the icons of each would bounce, just like Mail's, then stop, without the apps actually firing up). The crash logs revealed that those apps were also looking for this mysterious file, which apparently had somehow been misplaced/lost. I used the "Pacifist" program to reinstall the contents of that particular directory (using the Tiger install CD). Much to my relief, once that directory was reinstalled, the apps once again started up and worked normally. HOWEVER, I noticed some odd behavior with the Mail app. The first thing that became evident was that the Inbox did not show all the messages that had been there before. Looking under the ~/Library/Mail/POP-Dad's account/INBOX.mbox/Messages directory, however, it was clear that all the messages were indeed there (in the form of the individual .emlx files). They just did not seem to be displayed in the Inbox of the Mail app. I tried doing a "rebuild" of the mailbox, but this did not result in any additional messages being displayed. Any thoughts?
The other perplexing behavior is this: the Mail app on the eMac can send and receive mail, but, once you click on a newly-received (unread) message, and then go to another mail box (say, for example, the "Drafts" or "Sent" folders), and then return to the Inbox, the message that was just received is no longer displayed/listed in the Inbox. Once again, looking in the ~/Library/Mail/POP-Dad's account/INBOX.mbox/Messages directory reveals that the message IS there (again, in its own .emlx file), but is simply not being displayed in the Inbox. I can click on the individual .emlx files, and they open new windows in Mail, from which you can hit "reply" or "forward," as normal; it just won't display the actual message that was originally in the Inbox. Sent messages, however, seem to be saved/displayed normally.
I've searched through the Mail discussion forum, and while I've found discussions along generally similar lines, I have not located an entry dealing with these particular symptoms. As such, any input/suggestions would be greatly appreciated.
Thanks in advance for your time.
-Javier

Regarding the missing package that you reinstalled with Pacifist, it would have been better to fix the problem by reinstalling the Mac OS X 10.4.6 Combo Update. Actually, you're going to have to do that anyway, as the package you installed came from an older version of Mac OS X and could now be out-of-sync with the rest of the system. Not only that, but if there was something amiss with that package, chances are that something else went awry as well, so you should really reinstall the latest Combo Update. Read the following articles for guidelines on how to properly install system updates:
Troubleshooting installation and software updates
Installing software updates
Basically, you should verify/repair the boot volume (not just permissions) before installing the update, and no applications should be running while installing it.
As to the missing messages, the conversion from Mail 1.x to Mail 2.0 is broken. Take a look at the following thread to better understand the problem:
Help! "You need to take this account online in order to download it."
If you see a strangely named Messages-XXXXXX folder within any of the *.mbox folders in the Finder, that means the conversion didn't proceed as it should, so be careful about deleting the old files, as they may contain messages that didn't come through. Better just move them out of there if you wish.
I partially disagree with Allan (and with Ernie, who also has troubleshooted a lot of similar cases and believes the old files could still be troublesome after a successful conversion as well) in that I don't think the problem with Mail 2.0 is the presence of the old files, but rather that, as a result of the improper conversion, there is something wrong with Envelope Index and with some of the converted messages themselves. IMO, the old files shouldn't be a problem if the conversion worked properly. Mail should just ignore those files when it sees a proper Messages folder in the mailbox folder.
The reason you cannot see in Mail some messages for which an *.emlx file exists is precisely that there is something wrong with Envelope Index. Mail will simply ignore any *.emlx file for which a corresponding entry does not exist in Envelope Index. Actually, Mail doesn't look into the Messages folder at all when displaying the mailbox contents, it just loads whatever there is in Envelope Index. If that information is wrong, the information displayed by Mail will be wrong as well; it may refer to messages that no longer exist, ignore messages that do exist, display one message but load a different one when you open it, etc.
Re-creating Envelope Index without cleaning up the mailboxes first would probably fail and it could even make things worse, though. That's what makes troubleshooting these issues harder than it should be.

I just purchased an ipad and I can receive e-mail but I can't send or reply. I get a message that the e-mail is in the outbox because the server won't allow 'relaying.' What do I need to do?

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Contact whoever manages your email server and ask them what ports and security to use for SMTP from remote locations. ISPs and email admins often require different SMTP settings when sending email when not connected to the server's or ISP's network.

Mails/Alerts-triggered for messages stuck in queues and failed in moni

Hi,
I have two doubts.
1) Messages are getting stuck in smq2 of my ECC and PI system. I have to manually push them. Is there any mechanism in which we can get alerts/mails when messages get stuck in queues.
I have already gone through the blog /people/santhosh.kumarv/blog/2009/05/19/sap-xipi-alerts-for-queue-errors and I have implemented it in ECC system. But no mails were generated.
2)Is there any method in which I can get alerts/mails when a message fails in sxmb_moni of ECC system?
Thanks and regards,
Siji

Hi Sanjeev,
I made a report with the following code in it and executed it. So I think that should work even if the job for it is not scheduled. There were messages stuck in queue. But no alert was generated. I had also created alert category in ECC.
Thanks and regards,
Siji

Messages stuck in Outbox in Outlook

We are running Exchange 2007 SP1 and Outlook 2007 SP2.
We are increasingly recv'ing reports of users having messages stuck in the Outbox folder of their Outlook client. The messages are also visible in OWA, although the strange thing is that the messages do seem to have been delivered.
There seem to be a multitude of posts about this issue, but nothing concrete - does anyone know if MS has found a fix for this?
I can see this:
http://support.microsoft.com/kb/948984.
However, it states:
"In this scenario, when you log on to the online account that uses this personal folder, the Outbox folder indicates that there is a message that is waiting to be sent. This message is visible only in Outlook Web Access. The message is not visible in Outlook 2007"
- The difference is that we see this in Outlook 2007 as well.
Anyone?

Hi Yoshi,
1. Would you please let me know whether your customer has same scenarios described by the KB (Move Sent Items from OST to local PST file) when the issue occurs?
2. Whether the issue always occurs and can be reproduced? If the issue can be reproduced, please let me know the steps which reproduced the issue
3. If the issue can always be reproduced, please let me know whether the issue occurs if you use OWA to send email or use Outlook Online Mode to send email.
~~~~~~~~~~~~~~~~
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TechNet Subscriber Support in forum
If you have any feedback on our support, please contact [email protected]
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Mac Mail incoming messages stuck in endless loop

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First thing to do is never post your actual email address in the forums; you don't want to get lots of spam as a result of spambots harvesting that address.
Next, login to the web interface of your .mac account and verify how many messages are actually there, both new Unread messages, and already Read messages. Write those numbers down and then logout.
Quit Mail and go to Home/Library/Mail and remove the mailbox for your IMAP (.mac) account. Then delete any files that start with Envelope Index.
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Not likely.. the files from the card are loaded into the computer via iphoto I guess.. they are saved in a different format.. you cannot copy those files back to the camera card. But you should still have a backup of the photos .. in TM which is the backup of the iphoto library.
Almost nobody I have heard from will save the original files in raw format. To do that you would need to open the card via Finder and copy the raw files to a folder on the computer which you then backup by TM?? Is that how you have done it??
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Emails are "stuck" in my Apple Mail Outbox. I have deleted the account and reinstalled but still have the problem. Apple's "Network Diagnostics" report that it cannot connect to the SMPT server.

Emails are l "stuck" in my Apple Mail Outbox. I have deleted the account and reinstalled but still have the problem. Apple's "Network Diagnostics" report that it cannot connect to the SMPT server. TalkTalk (Tiscali) say there is no problem with their server because I have checked and can send emails with their webmail.

No that is not it:
Open Mail>Preferences>Accounts, the first page has this on it
If you click on the server name in the box (gmail in your case I assume) it opens and reveals this:
If you select Edit SMTP Server list you get this:
Post it here and, select the Advanced Tab (which looks like this)
Post this page as well.

Messages stuck in library/mail/outbox

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