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Mail sitting in Outbox with gear spinning on Sent

All of a sudden when ever I send an email and it could be 1KB it sits in the Outbox. I can shut down and restart Mail 10 times, and eventually it might be sent. Also the "gear" is always spinning on the Sent folder. If I click Check for mail, sometimes it works (send email) most of the time, I have to shutdown mail, and restart it a bunch of times for it to send the mail.

Any ideas?

-Paul S.

MacBook Pro 13.3" 2.53GHz, 8GB SDRAM, 250GB SATA (MB991LL/A), Mac OS X (10.6.4), 24-inch LED Cinema Display, iPhone 4 16GB, iPad 16GB WI-FI

Posted on Aug 31, 2010 7:15 PM

Reply
28 replies

Sep 1, 2010 6:50 AM in response to PaulSu

Same thing with me Paul, mine started about the time of the security update last month. Tried every thing I could think of, restoring Mail, then the .plist still was very flakey. Then the Ethernet stopped working. Tried everything there too in the networks area. Finally sadi the heck with it and took it into the Omaha Apple store to the "Genius". Took her about 15 min to check everything, delete bogus locations in Network and walla. She was moving so fast, hard to remember everything she did to straighten it out.

Jan 19, 2011 1:04 PM in response to PaulSu

I have found a fix for this!

First off, what didn't work:

1. Trashing the com.apple.mail.plist in ~/Library/Preferences/ did not work.
2. Trashing the ~/Library/Mail/ folder did not work.
3. Creating a new test user account and setting up the same account in Mail did not solve the problem.
4. Neither repairing disk structure nor repairing permissions in Disk Utility fixed the issue.
5. Deleting the email account in Mail->Preferences->Accounts and re-adding it did not fix the issue.

In fact, no combination of the above steps fixed the "spinning activity wheel next to the Sent mailbox problem".

I confirmed the email server settings both with the ISP, and by successfully setting the account up in Mail on several of the office machines running various iterations of 10.6. I also confirmed that the ISPs servers were viable and even logged into the service's Webmail portal to confirm the account worked properly in all aspects.

Before doing an Archive & Install with the installation disc I called Apple for advice. They confirmed that I had done all the usual troubleshooting steps noted above first and then gave me the following instructions:

1. Delete the application Mail from the Applications folder, drag its icon off the dock, then empty the trash.
2. Insert the OSX installation disc and, in the window that opens in Finder after the disc has mounted, double click the "Optional Installs" folder to open it.
3. Double click on "Optional Installs.mpkg" and after clicking through a bunch of default and informational screens - and entering your admin password once - you'll finally get to a list of the optional installs included with Snow Leopard.
4. Click the little triangle next to "Applications", then tick the box next to "Mail". Click "Continue" and finish the installation.

When done with step four, I attempted to open Mail but was treated to a little dialogue box that told me, in so many words, that this old version of Mail wasn't compatible with the newer version of Snow Leopard that was installed on my machine. I asked the Applecare person about this and she told me she'd seen this problem before. One last step was needed.

5. I went to http://support.apple.com/downloads/ and downloaded the latest OS combo update from the top of the "Featured Downloads" column on the left side of the page. (If you try to use Software Update instead, be aware that the automatic updates will not check the Mail version number separately from the version of OS X you're running, so manually downloading the combo updater is probably the only option).

Running the combo update on my system (even though I was already at 10.6.6) did the trick. Mail was updated and now opens with no issues. Not only that, but the spinning activity wheel problem is completely gone - I can now send and receive emails without grief.

Good luck!

Jan 20, 2011 2:34 PM in response to fredcortes

I find it amazing that Mail.app has such a serious problem. I can't tell you home many times I have been sending/replying to time sensitive email, only to have it shunted to Outbox.

When I have my speaker muted, I get zero warning that this has happened. (Outbox on my MBP only shows up if I kill and restart Mail.app.).

Once I get the angry call asking where my promised email is, I kill and restart Mail.app and there, much to my surprise, is often hours worth of messages that I have sent that have gone no where.

I find it amazing that (a) failed message deliveries are not made visible to the user immediately, and (b) that there appears to be no way to tell Mail.app to flush/retry the Outbox queue.

My conclusion is that Mail.app can't be used for business quality/critical email.

I am installing Thunderbird and moving on .... this is ridiculous.

dougm

Feb 11, 2011 2:17 PM in response to newks

Thanks so much for sharing this Newks.
My Mail has been spinning on sent all day and I have been searching the forums in despair.
Out of interest, it happened when I was on a client site and connected to their router. After that, I sent one message and then the spinning started.

So, I was just reaching for the installer disks, when all of a sudden I was prompted for my outgoing mail server password and it all sprang back into life.

But I have your info to hand, and hopefully will not need to use it!

Mar 14, 2011 10:52 AM in response to PaulSu

I've been having the same problem where mail sits in the outbox, undelivered, and have had at least one instance where work-related e-mails were delayed for hours because Mail didn't care to send them, with no warning.

In my case, Mail's activity viewer (command-0) shows connecting to SMTP server, forever. Occasionally, quitting and restarting Mail would send the stuck message, other times I'd have to open the message from the outbox and click send again.

Bravo to newks for providing what thus far appears to be a fix; I was so exasperated with this that I did the whole thing, including the 1 GB OS update. Still, this is an unacceptable bug, especially on a brand-new iMac with a clean, factory-installed OS.

Mar 16, 2011 4:23 PM in response to PaulSu

I am having this same problem with Mail. It started inexplicably this afternoon (3/16/11) after I had successfully sent and received emails earlier this morning. ???

It seems that I can receive mail OK. But hitting Send on written e-mails will put them into the Outbox, where they stay indefinitely. Connection Doctor shows the Internet connection is good ... connection to my e-mail account user/pass is good ... but Mail is not connecting to my SMTP server.

I did find that if I shut down my router firewall completely, I can send mail. That's the only workaround I've found, and it's not obviously not a fix.

No idea why this just all of a sudden started happening. Seems like there's a Mail bug in our midst, Apple!

Mail sitting in Outbox with gear spinning on Sent

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