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Level 1

6 points

Mail is getting stuck in my outbox?

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

Best reply

Linc Davis

Level 10

209,547 points

Posted on Jun 9, 2014 9:53 PM

Please follow these directions to delete the Mail "sandbox" folders. In OS X 10.9 there are two sandboxes, while in 10.8 there is only one. If you're running a version older than 10.8, this comment isn't applicable.

Back up all data.

Triple-click anywhere in the line below on this page to select it:

~/Library/Containers/com.apple.mail

Right-click or control-click the highlighted line and select

Services ▹ Reveal

from the contextual menu.* A Finder window should open with a folder named "com.apple.mail" selected. If it does, move the selected folder—not just its contents—to the Desktop. Leave the Finder window open for now.

Log out and log back in. Launch Mail and test. If the problem is resolved, you may have to recreate some of your Mail settings. You can then delete the folder you moved and close the Finder window.

This action will delete any custom Mail stationery that you have created. If you want to preserve it, ask for instructions.

If you still have the problem, quit Mail again and put the folder back where it was, overwriting the one that may have been created in its place. Repeat with this line:

~/Library/Containers/com.apple.MailServiceAgent

Caution: If you change any of the contents of the sandbox, but leave the folder itself in place, Mail may crash or not launch at all. Deleting the whole sandbox will cause it to be rebuilt automatically.

*If you don't see the contextual menu item, copy the selected text to the Clipboard by pressing the key combination command-C. In the Finder, select

Go ▹ Go to Folder...

from the menu bar and paste into the box that opens by pressing command-V. You won't see what you pasted because a line break is included. Press return.

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36 replies

JudeSh49

Level 1

13 points

Nov 7, 2015 2:23 PM in response to Hydro99

The fix by Linc Davis only worked for a while. This is obviously a recurring problem with the MacBook Air which Apple apparently is not interested in resolving (over 50,000 people have visited this Apple Support page to research this problems. I suspicion that there is a problem with AppleMail and its connection to the Internet. I only have this problem intermittently and it appears that the first emails which "clog" up the outbox usually has an attachment (of no particular size). Anyway, depending on whether I am going to move to a place with a stronger Internet connection, I "fix" it in one of two ways: I either delete the emails from my AppleMail outbox and cut/paste and resend them using their particular web page (e.g., if I am sending a Gmail email, I log onto Safari, go to Gmail and cut/paste the email from my AppleMail. and it sends immediately) Sometimes sending just one I'm this manner (the first one in the queue) will allow the others to be sent, but usually I have to cut/paste all of them. This is a real pain if you have allowed too many to get clogged up in your outbox. What always seems to solve the problem, however, is for me to go to an alternate physical location where the Internet connection is stronger (in my case, my office) and, viola' , they all go through. Logic tells me that it takes a stronger Internet connection to send emails from AppleMail on my laptop than it does from a Yahoo or Gmail site. This problem does not happen with my regular MacBook. By the way, sometimes connecting to the internet with my iPhone hot spot will provide me with a strong enough connection to break the clog in the AppleMail dam and send the emails. Good luck. I am so sick of this problem (because I enjoy working by remote from home) that I am tempted to return to using a laptop with a Windoes OS.

allenjd3

Level 1

4 points

Jun 10, 2016 11:23 AM in response to Hydro99

I tried Linc Davis's suggestion. Step one did not work, so I simply put the folder com.apple.mail back to its original location. But now I've lost every one of the folders I created under "On My Mac". Where did they go? Is there a way to retrieve these? All I did was move the folder to the desktop as instructed, log out, log back in, open mail, close mail, put folder back to original location, log out, log in, open mail. And all my folders were gone.

allenjd3

Level 1

4 points

Jun 10, 2016 11:24 AM in response to Linc Davis

allenjd3

Level 1

4 points

Jun 10, 2016 11:28 AM in response to BDSalop

Have you found a solution? This is a real problem for me too. I just lost years of email organization in a single click. it's got to be somewhere.

Nov 11, 2016 8:09 AM in response to Hydro99

I was a little nervous about trying the fix below. I still might try it if this keeps happening, but a workaround that worked perfectly for me was to open the email up from the outbox folder, then toggle the sender to a different account. In my case I have my .mac account (which by the way all three stuck emails were sent from...) toggled the sender pop-down to my google account, and voila, they finally sent themselves. So not really a fix, but a way to clear them out, if you have more than one email account set up.

Dec 7, 2016 8:16 AM in response to Linc Davis

I'm not sure if this is a safe solution for everyone. When I tried this, I'm not sure what it did with my "stuck" outgoing message, but it caused a pretty scary problem: It removed all the custom local mailboxes I use for long-term message storage. I had to force quit Mail, manually delete the com.apple.mail file that was automatically created in the Containers folder, and replace it with the one I had moved to the desktop. After a restart, my Mail returned to normal.

To fix the outgoing mail problem I found a much less radical solution at this location:

https://www.macambulance.co.uk/os-x-10-11-el-capitan-upgrade-mail-stuck-in-sendi ng-loop/

This simply advises you to remove Outbox.mbox from the V3/Mailboxes folder.

Mail is getting stuck in my outbox?