Help with e-mail getting stuck in Mail outbox

I recently ran into a problem where all the e-mails I tried to send in Mail got stuck in my outbox and were not sent. After reading posts on the Apple Support Communities website and doing some troubleshooting of my own within Mail, I reached a solution to the problem. When I first realized I could not send e-mail using a certain e-mail account of mine, since all e-mails were getting stuck in the outbox folder, I checked my available servers. I did this by opening the preferences window, clicking on the accounts tab, then clicking on the outgoing server pull-down menu. In the pull-down, I saw that the server I wanted to use was listed as "offline." To fix this problem and get the server back online so that I could send e-mail (as I could with my other account that was not listed as "offline"), I selected the outgoing server pull-down once again. In the menu, I selected "edit server list." On the page that pops up afterward, I highlighted the server I wanted to use. This way, I could see the information associated with the server. With this information in front of me, I realized that for some reason there was no password entered in the password field even though the "Authentication" setting was set to password. I entered my password associated with the e-mail account I was having problems with and "walla." The server was back online. I could send e-mails again without them getting stuck in the outbox!
This problem popped out all of a sudden for me and got me quite frustrated. I hope that this brief walk-through helps out some people out there having a similar issue. Best of luck!

That's one of the best walkthrough's i've read, thankyou!
However, I often have email stuck in the out box. And that's not comfortable… or good for communicating to clients.
In the hope that this may help someone:
Internet Connection Problem
A bit random but I found that by keeping an eye on the networked computers or the Dropbox icon tells me the health of my network or the internet connection that's causing a problem and all of the time, it's the Ethernet.
If networked computers are up and on the internet, but my PM isn't:
Solution:
1) Refresh the DHCP license.
2) Switch off the ethernet under system preferences/network then switch on again to refresh the IP addres.
Every time I do this, I find Apple Mail reconnecting straight away. I don't know why this happens.

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Mail gets stuck sending mail

I use Apple Mail on 3 different machines plus an iPhone. All the Macs are running Mavericks, and the phone is on the latest OS. My mail is a standard IMAP account. All my mail accessing (reading, sending, sorting, etc.) works perfectly on all devices except for my office computer:
On my office computer, when I send a standard mail with no attachment, it works perfectly. When I send a mail with an attachment, it stays in the Outbox for 30+ minutes, during which time no other mail is received. It's like the thing is jammed. After the 30+ minutes, the Outbox disappears, and Mail goes and receives all the mail that was received in those 30 minutes.
Having lived with this for a couple of months now, I have also learned that the mail in question is usually sent quickly (within 30 seconds) -- my recipients tell me they receive it. It's something *after* the mail is being sent that is jamming it up.
I opened up Mail's activity window, which shows several things going on, such as "updating cache directory" and "archiving copy to mailbox 'Sent Messages'" and "Copying 2 messages." I'm not sure which of these is causing the stuck-ness.
I've tried rebuilding the inbox, drafts, and sent mailboxes. This hasn't solved it.
This happened in 10.8 and is still happening in 10.9. Only on the office machine.
Does anyone know how to completely reset mail? Remove EVERYTHING about it and re-sync the whole thing from scratch? (Because my mail is IMAP this shouldn't cause any loss of mail.) I think it'd be best if I also remove all the Mail prefs too.

Looks like a configuration problem with your mail server. JavaMail did its job and got the
message to the mail server. Now it's up to the mail server to deliver it. Talk to your server
administrator.
Also, you could try authenticating to the mail server to see if that helps. See the JavaMail FAQ.

My outgoing mail gets stuck???, my outgoing mail gets stuck???

what to do, when your outgoing mail gets stuck in the outbox, the server comes up as offline...grr

I had this problem too but I fixed it today.
Go to the mail menu preferences.
Click on account in question.
Select the outgoing SMTP mail server (the one offline), this has a drop down list, click on the edit server list.
Click on the advanced button.
Make sure use default port is checked.
Make sure SSL is unchecked (unless your provider requires it, mine does not work with it checked).
Have authentication set to password.
User name should be your email address for that account.
Make sure correct password is entered (for some strange reason my password box was blank on this account).
Push the ok button.
For me the SSL box was checked and the password was missing. This is strange to me considering I have unchecked the SSL Box on the mail preference advance page. Also, I went through the complete set up account when I first created the account, why was my outgoing server password box empty?
I hope this helps.
Here is a link to some visual aids with the steps from my ISP
http://support.knology.net/content/smtpauth/smtpredirect.cfm

I am un able to send mail as it gets stuck in my outbox. I am sure the solution is simple but need help?

I am un able to send mail as it gets stuck in my outbox. This is a recent phenomena. I am sure the solution is simple but need help?

I looked everywhere for a solution - and I finally figured it out! Deleting my accounts didn't work, but here is what worked. This worked when my Gmail accounts were not sending properly. I'm not sure if it works for other e-mail services.
1. While in Mac Mail, click "Mail" in the top left corner of the screen
2. Click "Preferences"
3. Click "Accounts"
4. Select your account that isn't sending properly
5. In "Outgoing Mail Server (SMTP)" there will be two options - Gmail & Gmail (offline)
Make sure that "Gmail" is selected and NOT "Gmail (offline)"
If you navigate to another section in Preferences, it will ask you to SAVE - make sure you save your changes!
It worked for me, hope it works for you!

I just downloaded the new OS7 and now my e-mails are stuck in the outbox. I've tried several ways to send, with no luck. Help!

I just downloaded the new OSX 10.8.3 operating system, and now my e-mails are stuck in the outbox. I've tried to send various ways with no luck. Help!

Does the new IOS 8 and instagram only allow pictures taken with the phone? as I can still choose from those, just not the ones I upload/save.
I don't know about instagram, but apps, that not yet have been upgraded to iOS8 can only access the photos that appear in the "Recently Added" album, because there is no longer a Camera Roll.
As a work-around, try to create an album of the photos you want to share to instagram. For other apps this helped to make photos accesible.

Mail gets 'stuck' doing a send & receive

Hi,
Since upgrading to Mac OS 10.6.5, Mail regularly gets 'stuck' doing a send and receive. I have three IMAP mail accounts in Mail: one MobileMe and two GMail. I can't send any mail (messages get stuck in the Outbox). No new mail comes in. I can't Quit Mail. I can only Force Quit Mail (although the Force Quit app does NOT say that Mail is not responding - it thinks everything is OK). I use three Mail plugins: MailActOn, MailTags and Mail Attachments Iconizer. Neither restarting Mail or restarting my Mac helps - Mail just gets stuck again. I know it's an issue with the Mail software because other clients (e.g. Mail on iPhone and iPad) access my IMAP mailboxes just fine.
Here are some screenshots...
First, the Inbox and Sent folders have a continuously spinning wheel:
http://dl.dropbox.com/u/310720/spinning.jpg
Second, when I open Mail's Activity Viewer, you can see a whole heap of frozen processes (if I click any of the red "stop signs", they won't stop):
http://dl.dropbox.com/u/310720/activity.jpg
Does anyone have any tips?
Thanks,
Greg

After analysing Mail's Activity Viewer messages I thought perhaps Mail was getting stuck when downloading messages from my two POP accounts. I logged into both accounts via webmail and deleted the messages in there. Volia! Mail is now unstuck. This is clearly a serious bug in the program - why should a problem with messages in POP mailboxes cause the entire application (and all IMAP accounts) to freeze?
Cheers,
Greg

Can't send emails on my yahoo mail account. gets stuck in the outbox. tried deleting and reinstalling but it didn't work., can't send emails on my yahoo mail account. gets stuck in the outbox. tried deleting and reinstalling but it didn't work.

every time i try to send an email from my yahoo mail account it gets stuck in the outbox. i have tried reinstalling my email account but it doesnt work

Have you tried setting up your Yahoo account using Mac Mail instead of dealing with web based mail?
It only takes a minute to set this up.
Open Mac Mail. From the menu bar top of your screen click Mail > Preferences then select the Accounts tab then the Account Information tab.
Click +
Enter your name, Yahoo user name and password, click Create.
If you'd rather not do that, it would help to tell us which Mac OS X you have installed and which version of Safari in your reply.

Outgoing mail gets stuck in outbox?

Using MacMail. When sending mail, it seems to be getting stuck in the outbox for a long time. It gets sent to "onmymac" rather than the outbox for the particualr mail I'm using.

The solution below was found at: https://discussions.apple.com/thread/6351214
It appears to have solved the issue for me.
Linc Davis
Jun 9, 2014 9:53 PM
Re: Mail is getting stuck in my outbox?
in response to Hydro99
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.

Mail getting stuck in Outbox

I am using Outlook 2007 and exchange server. When send emails they oftentimes get stuck in the Outbox with a sent date of "None". If I restart outlook and try resending the messages, they will oftentimes go out. I am having to restart outlook 5 times a day right now. Any ideas what would cause emails going out through exchange server to just "get stuck"? Sometimes when I sent the emails and I watch the Outbox folder, the messages will appear in the outbox with a "sent" date, then after a second or so that "Sent" date will just change to "none" and the email just won't go out. Any advice on how to troubleshoot or fix?
One other note...some messages just NEVER go out 9regardless of how many times I hit restart outlook and hit send) and I need to rewrite them by creating a new message and sending and that new message.
NOTE: this appears to happen when I'm in a state where I am "Connected to Microsoft Exchange".

DontPanicZ wrote:
Hello,
I found a solution that worked for me.
See: http://www.slipstick.com/problems/outbox.htm
I followed the suggestions in the article and found that I had an add-in (that I did not need). When I disabled the add-in, my problem was solved.
Text of article follows:
After viewing the Outbox, the messages in it won't send.
If you click on the Outbox while messages are waiting to be sent, the messages are marked as read and won't send.
This is caused by a Net framework add-in you have installed that 'reads' Outlook items, including the Send to OneNote from Outlook PowerToy add-in and BCM (Business Contact Manager). A list of other add-ins known to cause this behavior is listed below.
To send the affected messages, you'll need to open the message, then switch to a different folder before clicking Send on the message. Do not go open the Outbox until after the messages are sent.
To identify the add-in that results in this behavior:
Look in Tools, Options, Other, Advanced, Com add-ins. Disable the add-ins and re-enable them one at a time and test.
Since BCM and possibly other add-ins are not listed in the COM add-in list, check
HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Office\Outlook\Addins
HKEY_CURRENT_USER\Software\Microsoft\Office\Outlook\Addins
Export the keys then change the LoadBehavior value to 0 to disconnect an add-in. Restart Outlook and test.
Applications responsible
The following is a list of some of the applications which are reported to cause message to be marked as read. If you use these or any other add-ins, check for a newer version - newer versions of some of these applications will not cause problems.
ICQExpress (COMAddin), installed as part of ICQ
Business Contact Manager (BCM)
Send to OneNote from Outlook PowerToy
Outlock
Outlook Backup Add-in
Sierra Wireless Outlook Integration - disable in the registry. It's listed at HKEY_LOCAL_MACHINE\SOFTWARE\Microsoft\Office\Outlook\Addins\SwiOutlookInt.Addin
ONFOLIO
Timeslips add-in
Attensa for Outlook. Check for upgrade: newer versions not affected.
Cisco Meetingplace plug-in
MindJet Mind Manager 6. Disable the add-in in the registry - the key is Mindjet.Mm6OutlookLinker.AddIn.2
Google desktop "search your own computer", specifically because it searches the mail
ScanSoft PDF Converter Outlook Addin
Norton AntiSpam Outlook Plugin
Norton Internet Security
AIM Sync
LinkedIn Outlook Toolbar
Salesforce
Upshot Outlook integration
MS CRM 3.0 Outlook Add-in
Xobni
Auto-Mate
RingCentral Add-in
DesktopSMS.Addin
More Information
If your mail won't send and it's not the problem described above, other possible causes are:
Authentication problems: Are you logging on to the mail server correctly?
No default mail account. If you can reply to messages but not send new message, check the account settings and make sure one is set as default. When you use a configuration script created by your mail provider or import accounts, an account is not always set as default.
See Email Won't Send - Common Causes for more information.

TS4062 HELP!!! When I try to sync my iPhone with iTunes it gets stuck at step 2 and goes no further. I have iTunes 10.6.3.25. It happens all the time. I have Windows 7.

Please help. Every time I try to sync my iphone with itunes it gets stuck at step 2 and just spins. I have iTunes 10.6.3.25 installed. I've even shut down and rebooted. Nothing helps.

Based on what someone else said, I am getting the "rotating ball of eternal sadness". Yup. That about describes it.

From time to time, my outgoing mail messages get stuck in the "outbox". I'm having trouble resolving the problem.

From time to time, my outgoing mail messages get stuck in the "outbox". I'm having trouble resolving the problem.

I use Comcast. My computer (Mac Air) also uses my iCloud and Me accounts. The message I get back says they are all offline.

HT3748 Messages sent through my Exchange Account with large attachments (10mb) get stuck in my Outbox.

I use Mail and icloud except at work. The wi-fi network at work won't allow icloud through so I use my work email setup on Mail as an Exhange account. When I have a large message (10mb) to send through this account it gets stuck in my Outbox and won't 'send'. It actually appears in the 'On my Mac' Outbox and not in the Exchange Outbox - even though i sent it using the Exchange account. IT at work are puzzled. This problem is only when at work - I can send through my Exchange account when I'm at home. Please help...

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.

Mails are stuck in the outbox after an offline period

Hi!
I am often writing e-mail while I'm offline, e.g. on planes, buses etc.
Then when I get back online I kinda expect the Mail App to send these mails instantly. However it does not do that. The mails are stuck in the outbox for up to 15-20 minutes after I get back online. The e-mails I have received while being offline are downloaded instantly as they should be. And if I then write new e-mails after getting back online they just get stuck in the same queue together with the other stuck e-mails.
Is there a fix for this? Do you experience the same? It is really annoying and making wonder if I should get another Mail App.
I have just installed the new Yosemite and I was hoping it had fixed the problem. But it hasn't...
I am working on a MacBook Pro 2013.
Thanks!

iOS does not run on MacBook Pros.
Drag the message to Draft mailbox and ensure the recipient is correctly addressed and send.

I have an itouch, most songs i got off my cd's. i have a new laptop and want to put songs from itouch to laptop.I can only get the songs that i purchased onto the laptop? need help with how to get the rest from itouch to laptop please??

i have an itouch, most songs i got off my cd's. i have a new laptop and want to put songs from itouch to laptop.I can only get the songs that i purchased onto the laptop? need help with how to get the rest of the songs (from my cd's) from itouch to laptop please??

See this previous discussion:
Recovering your iTunes library from your iPod or iOS device: Apple Support Communities

Emails are getting stuck in my outbox

We are using Outlook 2003 with a Gmail IMAP account. Everything was working fine until today when emails started getting stuck in my outbox. I used to be on an exchange server but have recently switched email accounts and added the IMAP to
my old outlook. What should I do so that i can send emails without them getting stuck?

Hi,
Maybe you are working Offline:
http://office.microsoft.com/en-us/outlook-help/switch-between-working-offline-and-online-HP005242598.aspx
http://office.microsoft.com/en-us/outlook-help/switch-between-working-offline-and-online-HP001232960.aspx#BM4
Or
A corrupted Outlook profile, please try creating a new Outlook profile for test:
http://support.microsoft.com/kb/829918
If it doesn’t work, check the configuration of Gmail in Outlook:
Please Note: Since the following web site is not hosted by Microsoft, the link may change without notice. Microsoft does not guarantee the accuracy of this information.
http://support.google.com/mail/bin/answer.py?hl=en&answer=77689
Sincerely
Rex Zhang
Rex Zhang
TechNet Community Support

Help with e-mail getting stuck in Mail outbox

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