Mail is getting stuck in my outbox?

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.

The receiving server might be rejecting the size of the attachment. Get a DropBox account and put your attachments online. Send the download link. The receiver does not need to have a DropBox account.

Another option with DropBox is to use a Shared folder. If you share files a lot with your friend, setup a Shared folder and everything in the folder will be shared. Obviously they also need to setup a free DropBox account (works on Windows). Just keep the folder size under the 2GB free limit.

For the future... OS X Yosemite Mail coming this fall, will offer a way to share files like DropBox.

Mail Drop allows you to attach large files via iCloud.

Attachments can be up to 5GB in size. -new feature in OS X 10.10 Yosemite Mail

Linc's reply looks good.

Didn't work for me however because...

Turns out it was down to our email hosting provider having recently implemented a server side change because of the new regulations surrounding SSL3.

We had to simply uncheck 'use SSL' on our outgoing IMAP SMTP settings and things were back to normal.

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Same issue here as well, on ancient Mac mini with latest version of OSX ( the mountainy one or the horsey one, not sure )......

I just moved the messages from the Outbox to a different folder, opened the messsages and resent them.

Maybe there is a handshake issue in the Outbox code, a queue implementation deficiency?

As soon as one gets stuck in the Outbox, they just back up,

Just empty the Outbox and resend them from another folder.

No point in fiddling about, not interesting and probably soon to be fixed.

Avraam Jack Dectis

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Just had this problem, and fix worked for me THANK YOU, but now i have 4396 "mails" in my inbox...i surmise this is a count of "all" mails saved in various folders (as opposed to truly "new" mails). Too, incoming mail pre directed to VIP mailboxes now no longer shows in the common inbox (as it did prior to the fix). This means I have to actively search these VIP folders for new mails. Any resolutions to these snafus? I am slightly above amateur with regards to these matters. Thank you in advance for any assistance or direction you are able to provide!!

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

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

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

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!

.

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.

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!!!!

🙂 🙂 🙂

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.

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.

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

This worked to get my mail "unstuck," BUT..

This action deleted all my mail folders - I certainly didn’t expect this to be a part of “your mail preferences will be deleted.”

Now all of the saved mail that I had sorted into folders is randomly in “all mail” - NOT good.

Would have been very helpful to point me EXPLICITLY at what "preferences" might be at risk in the original post! (We are not all as savvy..)

I thought this would be benign things like signatures, but all the organization in my mail is now GONE.

If there is some way to recover my file folder structure from the old "sandbox" file, it would be GREATLY appreciated.

I have not yet deleted the moved "sandbox" from my desktop.

Thanks for any suggestions.