Mail hangs in Outbox

Since I "upgraded" to Yosemite, emails often "hang" in the Outbox - sometimes for a minute, sometimes for an hour, sometimes for days.... and sometimes it's not a problem at all. Sometimes I can open the message in Outbox and resend it, but most often that doesn't work. Sometimes when a message has been in the Outbox all day, it will send when I restart the next morning. Sometimes the message will never be sent. This annoying post-Yosemite behavior affects all messages irregardless of length/size/content/attachments or lack thereof. One of my three accounts is most susceptible (a ".me" address), but all of the accounts fall victim to this glitch at least a few times a day. Any thoughts? Purge plist files?

Mail troubleshooting - Yosemite
What does Mail/Window/Connection Doctor Show? If the server is red, select it and look at the Show Details box.
Troubleshooting sending and receiving email messages
Troubleshooting sending email messages

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Having trouble with mail..Wheel spins and mail hangs up when mainly when sending

Having trouble with mail..Wheel spins and mail hangs up when mainly when sending

Have you many items in outbox? Seen this where a message has a large attachment and I stuck

Mail Hangs after 10.5.6 update

After installing the 10.5.6 update via Software Update Mail started to Hang. Odd, it worked for about a day then turned south, very south. I have no 3rd party add-ons. Simple set up to SBC global DSL via yahoo. I can't even create a new account because Mail hangs within 5-10 seconds of launch-beach ball and force quit. I have restored a pre update version of mail.app via Time Machine, but that does not change a thing. Kept both versions. I don't know what other elements could/should be restored from Time Machine to regain pre update functionality. Please, any suggestions.

After losing hours of my life trying to find an answer, I tried mucking around myself. Found that Time Machine can indeed restore Mail, or at least it did repair my problem. Rather than replacing Mail.app and main library files, which did nothing, I restored my 'User' Mail LIbrary ( 'damaged user Account' >Library>Mail ) to Sunday before the 10.5.6 update. Be sure to Import mailboxes from the splash screen Welcome to Mail Window that will appear when you relaunch Mail after TM restore, this will restore all the mail boxes as they were, otherwise everything is empty. I now will be archiving my mail diligently, I promise, even before the new year. Seems the 10.5.6 upgrade has caused many many problems in many many areas, Mail just being the one I was blessed with. Good Luck. Time Machine is Wonderful when it is on an external HD.

Mail hangs when it receives a report that an e-mail could not be delivered.

Hi Guys :o),
One bug which is really bugging me is that every time I receive a bounced e-mail report, with a subject line containing words to the effect of:
"Undeliverable. Return to sender."
or:
"The message could not be delivered."
Mail is unable to pull any subsequent e-mails down from the POP server.
So I junk the report, and then I delete it.
However, lo and behold, the errant e-mail is INSTANTLY back in my Inbox, plus there's now AT LEAST one copy in my Mail Junk, and also AT LEAST one copy in my Mail Trash.
Round and round I go, junk, delete, junk, delete, but the errant e-mail refuses to go away, and Mail continues to be unable to pull any new e-mails down from the POP server.
Eventually, Mail just hangs, with a spinning disk.
Even a force quit and relaunch of Mail doesn't resolve the spinning disk.
The errant message just sits there, REFUSING to be deleted.
The only way to get round this bug is for me to go up to my POP server, delete the report, and then PURGE DELETE the report - on the POP server !
I then have to go in to my Mac, and go:
--> Users --> Home --> Library --> Mail --> Account --> Inbox, Junk, and Deleted
and then manually drag ALL copies of the report into the trash on the Desktop.
It happens so often (pretty much every day) that I've had to create a shortcut in my Dock which leads straight to the Account folder.
Mail has always been buggy under ALL versions of OS X, but this ongoing bug drives me crazy, mainly because there's NO logical reason for it.
Just because I receive an e-mail message from the Hotmail server, for example, which says that my e-mail could not be delivered, usually because the recipient's inbox is full, or because no such address exists, on paper, that's just another e-mail which Mail is pulling down from the POP server.
However, EVERY TIME I receive such a report, Mail hangs.
I'm reluctant to rebuild my Mailboxes, in case I lose any messages, but I will if you advise it.
Any workaround would be gratefully received.
With best wishes to everyone in the Apple community, especially those on the Infinity Loop.
In particular, I wish Mr Jobs a very speedy recovery.
Cool,
Michael T
London, England

Quit Mail, Right click on that Mail folder, choose archive, you'll get everything in the folder, and the folder itself in a file called Mail.zip, move it to a safe place, same for the Mail Downloads folder... only the plist is separate.
/Users/YourUserName/Library/Preferences/com.apple.mail.plist
Not certain, but this can fix myriad Mail problems...
Safe Boot from the HD, (holding Shift key down at bootup), it will try to repair your Disk Directory while the spinning radian is happening, so let it go, run Disk Utility in Applications>Utilities, then highlight your drive, click on Repair Permissions, then move these folder & file to the Desktop.
Move this Folder to the Desktop...
/Users/YourUserName/Library/Caches/Mail/
Move this file to the Desktop...
/Users/YourUserName/Library/Mail/Envelope Index
Reboot.
If that doesn't do it and you can afford to redo all your Rules, try these & reboot...
/Users/YourUserName/Library/Mail/MessageRules.plist
/Users/YourUserName/Library/Mail/MessageRules.plist.backup

Sent Mail Not In Outbox

I am sending mail and I here the "swoosh" sound but I am not seeing the mail in the outbox. I am often getting warning (triangle gray) that I am over my limit and delete mail. I don't think I have a lot of mail so I find it strange.
Any help would be greatly appreciated.

FYI - you are confusing terms. The Outbox is where all messages pass during the sending process. If a message cannot be sent for whatever reason, it will remain in the Outbox mailbox.
A successfully sent message is moved to the account's Sent mailbox - for the account used to send the message if settings are to store sent messages or something doesn't go wrong with this process.
What TYPE of account is this - .Mac, IMAP or POP?
If a .Mac or IMAP account, are you storing sent messages on the server or locally on the hard drive which is available under the Special Mailboxes tab for the account preferences?

I have old QuickMail Pro on my old iMac OS 9. Can Quick Mail's inbox, outbox and sent mail be downloaded onto an external hard drive?

I have QuickMail Pro on my old iMac OS 9. Can Quick Mail's inbox, outbox and sent mail be downloaded onto an external hard drive? If so, how? I tried to drag and drop but that didn't work.

Ok, best to contact itunes then so they can look into it

APPLE PLEASE HELP! Mail hangs after start, address book never launches!

I've been reviewing postings since friday last week about issues with mail/address book after 10.5.2 and here's a summary:
• Symptom 1: Mail launches slow
• symptom 2: mail hangs while downloading new mail (in my case from 1 particular account according to the activity viewer, while downloading the last, most recent msg, the msg does not have attachments but it stays downloading forever, force quit required)
• symptom 3: mail does not send msgs (in my case it sends one-by-one after each force quit/relaunch)
• symptom 4: duplicate msgs appear, particularly msgs received after 10.5.2
• symptom 5: mail does not quit,, force quit necessary. in my case after i force quit/ relaunch several times mail launches somewhat "normal" but after a reboot or relaunch, problems appear again. (duplicates never go away)
• issues with mail after 10.5.2 are not ISP/email host related, we all have different ISPs and hosts and we all have the same symptoms.
• i also experienced problems with address book, it starts but the window never opens or if it does is completely empty, no functions are possible. this also affected ichat as the info for the contacts cant be retrieved from address book.
thanks for reading and please contribute to the thread if you agree with the summary, APPLE NEEDS TO HELP US!!!

Hi everybody,
I have received an update from my friend who suffered from the Mail problem. In fact, the errors occurring AFTER the restore from Time Machine were due to an ISP's problem. So the restore really worked after all.
So to put it in a nutshell, I would recommend the following process:
1. Quit (or force-quit iff necessary) Mail asap when the application gets stuck. Do not open Mail again.
2. Restore ~/Library/Mail folder from the youngest Time Machine Backup you know Mail was behaving properly.
3. Run the 10.5.2 Combo Updater while all applications are shut down (just to be on the safe side).
4. After the inevitable Restart, check Software Update for more updates and install if necessary.
5. Run Mail and let it rebuild all the Mailboxes.
This should work fine to solve the problem. With the AddressBook case, I should try a similar workflow to get it fixed, yet I haven't tried that one so far.
BTW: I can only encourage you to really get an external drive and use Time Machine frequently. Even if it seems to be expensive in the first place, imho TM is the best piece of software Apple has been inventing for ages. In my case, I also tried to save money and took a leftover 40 gig HD from an old server and got myself a usb-2.0 external box for around 10 euros. Although space is limited, i have been backing up hourly since 1 February and there's still 12 gig to go. I only back um my home directory, as all my personal data, settings and mail are stored there.

Mail hangs when trying to open excel file

Hi there,
I've installed goodreader, Docs to Go and numbers on my ipad. Unfortunately, mail hangs when i try to open a spreadsheet. The option to use either one of the apps pops up, however, i'm not able to select either numbers or Docs to Go to open the file.
I've restarted the ipad to no avail. Does anyone have any ideas about this?
Thanks
Message was edited by: Sininakl

Running disk repair a second time seems to have fixed the issue.

Mail sits in outbox and doesn't send

mail sits in outbox and doesn't send

remember there is both a mail Sender and a mail Receiver. Receiver setup information is easy to find, but Sender setup information is a little harder to find.
Use exactly the settings your ISP provided, or use this Apple Mail Setup Assistant. (rest assured, Apple does not use this to collect your email address.)
https://www.apple.com/support/mail-settings-lookup/
The easy-to-see info in Mail preferences is for your Mail Receiver. This corresponds to the top part of the box from the Apple site.
You need to use Connection Doctor and click on the red light to get easy access to the Mail Sender info. This corresponds to the bottom part of the box from the Apple site.

Mail hanging

Since updating to Lion, Mail hangs for ever while trying to retrieve messages. I have my iPhone connected to my iMac all the time whilst I am in my study, and I can hear the alert telling me when new mail arrives on my phone but when I go to Mail it won't retrieve new messages until I Quit and relaunch it. (Just the latest in a long line of issues I've had since updating to Lion...)

with regard to my question:
Mail hangs on start and I have to force quit to get out of it. The question was answered from another person running 10.4 Here was the response:
will this work for 10.3.9
The Mail.app preference file may have some corruption.
With the Mail.app quit and using the Finder, go to Home > Library > Mail. Copy the Mail folder and place the copy on the Desktop for backup purposes.
Using the Finder, go to Home > Library > Preferences > com.apple.mail.plist. Move the com.apple.mail.plist file to the Desktop.
Note: When moving the com.apple.mail.plist file out of the Preferences folder will require re-entering all email account information when re-launching Mail.
The only exception will be a .Mac account which should be re-entered automatically.
Launch Mail and deline any prompt to import mailboxes. As required, after re-entering all email account information the Mail.app should rediscover the existing account named folder(s) and mailboxes at Home > Library > Mail.
If this is successful and after confirming all mailboxes were successfully rediscovered, you can delete the copy of the Mail folder and old com.apple.mail.plist file from the Desktop.

Mail hangs when downloading messages from Exchange

I've had the problem of Mail hanging when downloading from Exchange 2007, though from time to time it all works fine, suggesting all the settings are correct. Sometimes it will all work after a few forced quit- restart cycles, but this isn't reliable. Following advice on this forum I've trimmed the number of messages on the server (to c. 3,500), to no effect, and have deleted the Envelope Index file (which did temporarily alleviate the problem, but issues returned 24 hours later).
I see several errors are reported to Console which suggest a communication problem with EWS, and in particular an "id" issue, ("id is malformed" and a illegal temporary id is being used online) though I have no idea what id this is, or whether I can influence it in any way. Here are three exemplars:
1)
04/01/2010 00:27:10 Mail[14116] * Assertion failure in -[EWSGateway resolvedIdStringForIdString:], /SourceCache/Message/Message-1077/MessageStores.subproj/EWSGateway.m:1548
Temporary ids should never be used while online. Got temp-e2dbcc09-254b-4f02-9a54-05e314cb0755.
0 Message 0x00007fff82691119 -[MFAssertionHandler _handleFailureWithPreamble:description:arguments:] + 137
1 Message 0x00007fff8269107e -[MFAssertionHandler handleFailureInMethod:object:file:lineNumber:description:] + 220
2 Message 0x00007fff825dcb68 -[EWSGateway resolvedIdStringForIdString:] + 186
3 Message 0x00007fff825da29d -[EWSDeleteItemsRequestOperation prepareRequest] + 380
4 Message 0x00007fff825f1f93 -[EWSRequestOperation executeOperation] + 60
5 Message 0x00007fff8269f347 -[MonitoredOperation main] + 229
6 Foundation 0x00007fff8800406d -[__NSOperationInternal start] + 681
7 Foundation 0x00007fff88003d23 ___startOperations_block_invoke2 + 99
8 libSystem.B.dylib 0x00007fff87cb0ce8 dispatch_call_block_andrelease + 15
9 libSystem.B.dylib 0x00007fff87c8f279 dispatch_workerthread2 + 231
10 libSystem.B.dylib 0x00007fff87c8ebb8 pthreadwqthread + 353
11 libSystem.B.dylib 0x00007fff87c8ea55 start_wqthread + 13
3)
04/01/2010 00:27:11 Mail[14116] * Assertion failure in -[EWSResponseOperation handleResponseMessage:withObject:], /SourceCache/Message/Message-1077/MessageStores.subproj/EWSResponseOperation.m: 420
Mail did something wrong: Id is malformed. on EWS response <EWSResponseOperation: 0x1168c57a0> (EXECUTING)
0 Message 0x00007fff82691119 -[MFAssertionHandler _handleFailureWithPreamble:description:arguments:] + 137
1 Message 0x00007fff8269107e -[MFAssertionHandler handleFailureInMethod:object:file:lineNumber:description:] + 220
2 Message 0x00007fff825f2eb2 -[EWSResponseOperation handleResponseMessage:withObject:] + 2295
3 Message 0x00007fff825f3592 -[EWSResponseOperation handleResponseMessages] + 240
4 Message 0x00007fff825f30a1 -[EWSResponseOperation executeOperation] + 69
5 Message 0x00007fff8269f347 -[MonitoredOperation main] + 229
6 Foundation 0x00007fff8800406d -[__NSOperationInternal start] + 681
7 Foundation 0x00007fff88003d23 ___startOperations_block_invoke2 + 99
8 libSystem.B.dylib 0x00007fff87cb0ce8 dispatch_call_block_andrelease + 15
9 libSystem.B.dylib 0x00007fff87c8f279 dispatch_workerthread2 + 231
10 libSystem.B.dylib 0x00007fff87c8ebb8 pthreadwqthread + 353
11 libSystem.B.dylib 0x00007fff87c8ea55 start_wqthread + 13
3)
04/01/2010 11:25:57 iCal[9798] deleting pending creates because the server failed to confirm their creation: (
"<NSManagedObject: 0x115cf0a50> (entity: ContactMapping; id: 0x1185962f0 <x-coredata://54D56B92-4C67-416D-8B08-A79AB7FDAF86/ContactMapping/p361> ; data: <fault>)",
"<NSManagedObject: 0x115c4e530> (entity: ContactMapping; id: 0x115ce7bc0 <x-coredata://54D56B92-4C67-416D-8B08-A79AB7FDAF86/ContactMapping/p362> ; data: <fault>)"
Any help very welcome!

I finally called AppleCare again (after the first rep never got back to me), and we determined that somehow my Mail Rules had become corrupted. One of them (probably thanks to OmniFocus fiddling with my Mail rules) was caught in a loop that would keep repeating until it caused Mail to crash. I had to remove the "MessageRules.plist.backup" and "MessageRules.plist" files from my ~/Library/Mail folder, and then recreate all my rules, but that did the trick.

TS3276 Help - Mail is not sending or receiving any e-mails . Connectivity Doctor is showing green lights.Have rebooted but same issue - just a circle continually going around the Sent mailbox and 2 e-mails waiting in Outbox.

Help - Mail is not sending or receiving any e-mails . Connectivity Doctor is showing green lights.Have rebooted but same issue - just a circle continually going around the Sent mailbox and 2 e-mails waiting in Outbox.

Is your web browser working normally?

2 Mails stucked in outbox and can not delete them..

Hi I'm Daniel, I have a problem with my mail app on my mac, last week i tried to send 2 videos using mail drop but my application wasn't working at all, i close the application and send the videos using googledrive but now when I open my mail app theres 2 mails on the outbox and I CAN NOT DELETE THEM its frustrating because every time i click on the mails and select delete my mac gets stuck and i have to shut it off with the power botton. I tried to delete my mail accounts and put them back on, but it doesn't work at all, i tried to remove some folder that i saw in another discussion here but it doesn't work, please help me!

The links below have instructions for deleting photos.
iOS and iPod: Syncing photos using iTunes
http://support.apple.com/kb/HT4236
iPad Tip: How to Delete Photos from Your iPad in the Photos App
http://ipadacademy.com/2011/08/ipad-tip-how-to-delete-photos-from-your-ipad-in-t he-photos-app
Another Way to Quickly Delete Photos from Your iPad (Mac Only)
http://ipadacademy.com/2011/09/another-way-to-quickly-delete-photos-from-your-ip ad-mac-only
How to Delete Photos from iPad
http://www.wondershare.com/apple-idevice/how-to-delete-photos-from-ipad.html
iPhoto for iOS (iPad): Delete photos from iPhoto
http://support.apple.com/kb/ph3137
How to: Batch Delete Photos on the iPad
http://www.lifeisaprayer.com/blog/2010/how-batch-delete-photos-ipad
(With iOS 5.1, use 2 fingers)
How to Delete Photos from iCloud’s Photo Stream
http://www.cultofmac.com/124235/how-to-delete-photos-from-iclouds-photo-stream/
 Cheers, Tom

Outlook 2013 mail stuck in Outbox

We just started using Outlook 2013 and Exchange 2013 (Fresh install) but we got a problem with additional mailboxes.
When you open additional mailboxes on your exchange account settings where you have send as permissions and full access and then send an e-mail from that mailbox it stays in the outbox. Sending an e-mail in owa works fine from the mailbox.
What can this be?

We need to try basic steps for this mail stuck in outbox issue as below:
Work offline, move the stuck mail into another folder. Restart Outlook and Work online to send it again.
Temporarily uninstall or disable firewall and antivirus software.
Test in Outlook safe mode.
Create a new profile and re-setup your account.
Let me know the resualt. Thanks.
Tony Chen
TechNet Community Support

Mail stays in Outbox

I know at least four people who are having this problem as well as myself and each of us has a different Internet host, but all of us started experiencing this problem when we upgraded to Tiger OSX 10.4.8. WE can receive mail just fine, but when we send an email, it just goes to the Out box and sits there. When we run connection doctor, we are told that our Macs are communicating with SMTP and other servers just fine. And we don't get any error messages. Just mail that sits in the outbox. We've all gone to our respective Internet providers and gone through the rigamarole of resetting from Port 21 to 547 and back again. Two of us have done a clean install of System 10. Still no dice. WE can all send mail just fine with Yahoo mail and to make matters even more mysterious, I can send mail from my laptop going through my same account and mail servers. It's just my desktop Mac that's having the problem (although my friend tried to login and send on his laptop through airport to our internet connection and was NOT able to send mail.)
Help
G5 Power Mac Mac OS X (10.4.8)

Mail silently (i.e. with no error message provided) going to the Outbox and sitting there would be typical of an account that's "offline", but I assume that's not the case, i.e. Mailbox > Go Online is disabled (grayed out), right?
I wonder whether this could be some form of index corruption. You may want to try the following and see whether it makes a difference:
1. In Mail, move any messages that may still be in Outbox out of there, to some other mailbox.
2. Quit Mail.
3. In the Finder, go to ~/Library/Mail/. Make a backup copy of this folder, just in case something goes wrong -- e.g. by dragging it to the Desktop while holding the Option (Alt) key down.
4. Locate Envelope Index and move it to the Trash. If you see an Envelope Index-journal file there, delete it as well.
5. In the Finder, go to ~/Library/Mail/Mailboxes/, locate Outbox.mbox and move it to the Trash.
6. Open Mail. It will tell you that your mail needs to be "imported". Click Continue and Mail will proceed to re-create Envelope Index -- Mail says it's "importing", but it just re-creates the index if the mailboxes are already in Mail 2.x format.
Note: For those not familiarized with the ~/ notation, it refers to the user's home folder, i.e. ~/Library is the Library folder within the user's home folder.

Mail hangs in Outbox

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