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Q: Mail is getting stuck in my outbox?

Hi

 

I've got a 13" Macbook Air that's about 12 months old. It's got a 1.7ghz I7 processor and 8GB of RAM.  About 2-3 weeks ago I started having intermittent issues sending email where my mail just sits in the outbox and doesn't send. I'm using the Apple Mail client and have an iCloud email account, although I'm still using the @me.com domain for the email.

 

I've checked the Connection Doctor. I get green lights all the way through and it says "Connection to server and login succeeded", but my emails still aren't sending. I can't be certain of this but it seems more likely to happen when I send something with an attachment. The emails would be under 10mb still.

 

If I try quitting mail from Mail>Quit Mail the email application won't close.  if I try to quit by right clicking on it in the menu bar it won't close either. I have to use "Force Quit" off the apple menu to shut the application down.

 

As an example, looking at the emails stuck in there at the moment there's three. The first one I tried to send at 9:21am. It's now 10:38am and it still hasn't gone. I've checked my internet connection and I'm getting 4mb/sec download and 1.7mb/second upload. So not crazy fast but more than enough to send three emails.

 

I've tried removing the account and adding it again. This took ages to download all my emails locally again but didn't fix any of the problems.

 

Any suggestions?


MacBook Air, OS X Mavericks (10.9.3)

Posted on Jun 9, 2014 7:57 PM

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Q: Mail is getting stuck in my outbox?

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  • by caxiduque,

    caxiduque caxiduque Jan 12, 2015 3:13 AM in response to Linc Davis
    Level 1 (0 points)
    Jan 12, 2015 3:13 AM in response to Linc Davis

    This solution worked for me.

    One more reason not to upgrade from an old version but instead go and do a clean install.

    Made this mistake myself moving from mavericks to yosemite directly instead of a clean install... so have been struggling with different errors..

     

    Thank you Linc Davis

  • by JBinKC,

    JBinKC JBinKC Jan 19, 2015 5:10 PM in response to Linc Davis
    Level 1 (0 points)
    Jan 19, 2015 5:10 PM in response to Linc Davis

    This enabled me to get my wife's Apple Mail back in operation after several days of mail stacking up in her outbox.  Thank you!

    Comments:

    1.  I wasn't clear what the "sandbox" referred to, but as I far as I can tell this didn't hamper my success in getting her outbound mail flowing again.

    2.  I had to move both files .mail and .mailserviceagent to succeed. 

    3.  We're running OSX 10.1.1 Yosemite.

    4.  The only visible impact we've seen so far was thel oss of her customized Mail toolbar, but that was no big deal.  She doesn't use custom stationery.

     

    Thanks again,

    JB

  • by ADG UK,

    ADG UK ADG UK Feb 1, 2015 7:52 AM in response to Linc Davis
    Level 1 (0 points)
    Feb 1, 2015 7:52 AM in response to Linc Davis

    Everyone else seems to have solved this - but not me on my nice new 5k iMac - I have messages stuck in my outbox

     

    I am on: Yosemite 10.10.2, using Mail 8.2 with an IMAP account from Virginmedia

     

    So far I have:

    1) Checked the smtp server settings - port '465' with SSL 'ticked' and authenticated with 'Password'

    2) Checked I the advanced settings on the account: port 993 with SSL 'ticked'

    3) Checked the Connection Doctor is all green for smtp and virginmedia

    4) Checked mails send from my iPhone (and they do)

    5) moved both files - apple.com.mail and apple.com.mailserviceagent to the desktop

    6) rebooted the mac and rebooted the wifi in the house

     

    I did have one mail get sent but I have 2 small mails still stuck.

    Any advice welcome please - thanks in advance

  • by JBinKC,

    JBinKC JBinKC Feb 1, 2015 1:50 PM in response to JBinKC
    Level 1 (0 points)
    Feb 1, 2015 1:50 PM in response to JBinKC

    Turns out this was only a temporary fix (the steps outlined above).

     

    Next, I upgraded to the new OSX 10.2.2.  Sadly, this did not fix the problem either.

     

    Next, I deleted the iCloud Account on the computer.

    Rebooted.

    Then reinstalled an iCloud account, and waited a while for the mailboxes on the computer to be repopulated from the Cloud.

     

    And - Good News - the Mail has been working properly since (36 hours).

     

    Good luck!

    .

  • by ADG UK,

    ADG UK ADG UK Feb 4, 2015 2:50 PM in response to JBinKC
    Level 1 (0 points)
    Feb 4, 2015 2:50 PM in response to JBinKC

    Thank you!

    I had two mail accounts - one iCloud and one from Virginmedia.  Your approach of deleting and reinstalling didn't work first time, but I tried again - this time with iCloud first and I didn't select to share the 'keychain' access iniCloud as I thought this might be polluting the set up some way from the other mac in the house which isn't upgraded to Yosemite yet.

     

    The good news it worked! I don't know why and I haven't turned 'keychain' access back on yet - but it is great to have email back.

     

    Many many thanks.

  • by Buffyslayfan,

    Buffyslayfan Buffyslayfan Feb 12, 2015 6:55 AM in response to Linc Davis
    Level 1 (0 points)
    Feb 12, 2015 6:55 AM in response to Linc Davis

    Thank you Linc for posting this because this is the only thing that worked for me. I know what caused the problem and I don't really know exactly what I did to solve it but I followed your instructions and the second option worked for me.

    Thank you again!!!!

     

     

  • by Lounger,

    Lounger Lounger Mar 5, 2015 3:27 AM in response to Linc Davis
    Level 1 (4 points)
    Mar 5, 2015 3:27 AM in response to Linc Davis

    Hi Linc,

    the problem did return, I am hoping that your second  solution,  works.

    Thanks,

  • by catnk9,

    catnk9 catnk9 Mar 16, 2015 5:40 PM in response to Linc Davis
    Level 1 (0 points)
    Mar 16, 2015 5:40 PM in response to Linc Davis

    Thank you. I had to do the second fix of moving the folder, but it's worked so far! Here's crossing my fingers....

  • by exyfeplin,

    exyfeplin exyfeplin Apr 1, 2015 10:32 PM in response to Linc Davis
    Level 1 (0 points)
    Apr 1, 2015 10:32 PM in response to Linc Davis

    This advice seems to have fixed my problem.

     

    However after deleting ~/Library/Containers/com.apple.mail, my preferences were reset (as expected), but none of the changes that I made would be retained after Mail had been shut down restarted.

     

    The way to fix that problem was to repair permissions on my system disk, using Disk Utility after booting from the Recovery HD.  Using Disk Utility in the normal way didn't fix the problem.

  • by Surge74,

    Surge74 Surge74 Apr 28, 2015 6:52 AM in response to exyfeplin
    Level 1 (10 points)
    Apr 28, 2015 6:52 AM in response to exyfeplin

    Moved both files and it did not work.

     

    Have been having a lot of issues with Mail on Yosemite.  It's really a POS.

     

    Had NO issues with 10.7's Mail, and now I have spent countless hours trying to sort through Mail crashing on launch (which is still does), and now emails sitting in the Outbox.  What a joke this is.

  • by virologist,

    virologist virologist May 4, 2015 7:13 AM in response to Linc Davis
    Level 1 (0 points)
    May 4, 2015 7:13 AM in response to Linc Davis

    Thanks very much! Same problems, resolved! It works!

  • by nlmillervt,

    nlmillervt nlmillervt May 5, 2015 3:07 PM in response to Linc Davis
    Level 1 (0 points)
    May 5, 2015 3:07 PM in response to Linc Davis

    This has been a problem ever since I upgraded to Yosemite last fall. So far the first part of the solution seems to be working for me.  Thanks!

  • by Chez70,

    Chez70 Chez70 Jun 21, 2015 11:21 AM in response to Linc Davis
    Level 1 (0 points)
    Jun 21, 2015 11:21 AM in response to Linc Davis

    Thank you, Link.  I had my email stuck in outbox for TWO days and finally found your solution and it worked on my OS X Yosemite 10.10.3!!  I am very happy to have MAIL back in business- Kudos.  Chez 70

  • by grbenson,

    grbenson grbenson Aug 17, 2015 7:15 PM in response to Linc Davis
    Level 1 (0 points)
    Aug 17, 2015 7:15 PM in response to Linc Davis

    Thank you!!!!  It worked great.

  • by celiarias,

    celiarias celiarias Aug 27, 2015 3:51 PM in response to Linc Davis
    Level 1 (0 points)
    Aug 27, 2015 3:51 PM in response to Linc Davis

    I've done all of these steps and still can't get mail to send out of the outbox   :/

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