I understand that you are unable to send emails in Outlook 2010. The emails got stuck in the Outbox.

Based on the current situation, this issue can be caused by several factors, such as Internet connection, Outlook settings or corrupted outlook profile. We can try the following methods to see if the problem can be resolved.

Method 1:

====================

Click the “Send/Receive” tab, then click “Send all”.

Method 2: New Outlook profile

==============

1.            Exit Outlook.

2.            Go to Start > Control Panel, click or double-click Mail.

Mail appears in different Control Panel locations depending upon the version of the Microsoft Windows operating system, Control Panel view selected, and whether a 32- or 64-bit operating system or version of Outlook is installed.

The easiest way to locate Mail is to open Control Panel in Windows, and then in the Search box at the top of window, type Mail. In Control Panel for Windows XP, type Mail in the Address box.

Note    The Mail icon appears after Outlook starts for the first time.

The title bar of the Mail Setup dialog box contains the name of the current profile. To select a different existing profile, click Show Profiles, select the profile name, and then click Properties.

3.            Click Show Profiles. Choose Prompt for a profile to be used.

4.            Click Add.

5.            Type a name for the profile, and then click OK.

6.            Start Outlook, and choose this new profile.

7.             Try to send the emails in the new profile

• Marked as answer by Sally Tang Tuesday, March 16, 2010 1:55 AM

I understand that you are unable to send emails in Outlook 2010. The emails got stuck in the Outbox.

Based on the current situation, this issue can be caused by several factors, such as Internet connection, Outlook settings or corrupted outlook profile. We can try the following methods to see if the problem can be resolved.

Method 1:

====================

Click the “Send/Receive” tab, then click “Send all”.

Method 2: New Outlook profile

==============

1.            Exit Outlook.

2.            Go to Start > Control Panel, click or double-click Mail.

Mail appears in different Control Panel locations depending upon the version of the Microsoft Windows operating system, Control Panel view selected, and whether a 32- or 64-bit operating system or version of Outlook is installed.

The easiest way to locate Mail is to open Control Panel in Windows, and then in the Search box at the top of window, type Mail. In Control Panel for Windows XP, type Mail in the Address box.

Note    The Mail icon appears after Outlook starts for the first time.

The title bar of the Mail Setup dialog box contains the name of the current profile. To select a different existing profile, click Show Profiles, select the profile name, and then click Properties.

3.            Click Show Profiles. Choose Prompt for a profile to be used.

4.            Click Add.

5.            Type a name for the profile, and then click OK.

6.            Start Outlook, and choose this new profile.

7.             Try to send the emails in the new profile

• Marked as answer by Sally Tang Tuesday, March 16, 2010 1:55 AM

I understand that you are unable to send emails in Outlook 2010. The emails got stuck in the Outbox.

Based on the current situation, this issue can be caused by several factors, such as Internet connection, Outlook settings or corrupted outlook profile. We can try the following methods to see if the problem can be resolved.

Method 1:

====================

Click the “Send/Receive” tab, then click “Send all”.

Method 2: New Outlook profile

==============

1.            Exit Outlook.

2.            Go to Start > Control Panel, click or double-click Mail.

Mail appears in different Control Panel locations depending upon the version of the Microsoft Windows operating system, Control Panel view selected, and whether a 32- or 64-bit operating system or version of Outlook is installed.

The easiest way to locate Mail is to open Control Panel in Windows, and then in the Search box at the top of window, type Mail. In Control Panel for Windows XP, type Mail in the Address box.

Note    The Mail icon appears after Outlook starts for the first time.

The title bar of the Mail Setup dialog box contains the name of the current profile. To select a different existing profile, click Show Profiles, select the profile name, and then click Properties.

3.            Click Show Profiles. Choose Prompt for a profile to be used.

4.            Click Add.

5.            Type a name for the profile, and then click OK.

6.            Start Outlook, and choose this new profile.

7.             Try to send the emails in the new profile

• Proposed as answer by JonMicroman Friday, October 18, 2013 3:15 PM

• Proposed as answer by JonMicroman Friday, October 18, 2013 3:15 PM

I wouldn't call this a solution, rather a workaround. I would be happier if there was a hotfix for this, as obviously there is a problem with Outlook 2010.

I might also add that i have the same problems, and i use CheckPoint client (had to disable security policy before when i had problems with outlook 2007).

forgot to mention that aprox 90% of our users are still using Outlook 2003 - they do not experince any problems - our mail server i exchange 2010 - I know the protocol used by clients to communicate with the server is different from 2003 to 2010, so giving the fack that Outlook 2003 does not have problems, does not exclude the server from having configurations isues

I do how-ever admit that the most likly place to look is at the client side (since it works for some users)

None of our Outlook 2010 kcients are installede by hand, they are all pushed to the client the same way, so they should behaive the same....

• Proposed as answer by brumple Friday, February 04, 2011 3:36 PM

forgot to mention that aprox 90% of our users are still using Outlook 2003 - they do not experince any problems - our mail server i exchange 2010 - I know the protocol used by clients to communicate with the server is different from 2003 to 2010, so giving the fack that Outlook 2003 does not have problems, does not exclude the server from having configurations isues

I do how-ever admit that the most likly place to look is at the client side (since it works for some users)

None of our Outlook 2010 kcients are installede by hand, they are all pushed to the client the same way, so they should behaive the same....

• Proposed as answer by brumple Friday, February 04, 2011 3:36 PM

Yes, seam like a common problem, might not only be a outlook client problem, but could also be a server setting witch are incorrect/missconfigured.

We experince the same - some of our users we have upgraded to Office 2010 and from time to time they experince mail delayed in the outbox - mostly the same users (daily)

We have tryed to delete/re-create the Outlook profile, but apparently this does not do the trick - could this be server side related ?

(in general out network is fast, so I do not suspect network or routing problems)

if anyone found a solution please share

forgot to mention that aprox 90% of our users are still using Outlook 2003 - they do not experince any problems - our mail server i exchange 2010 - I know the protocol used by clients to communicate with the server is different from 2003 to 2010, so giving the fack that Outlook 2003 does not have problems, does not exclude the server from having configurations isues

I do how-ever admit that the most likly place to look is at the client side (since it works for some users)

None of our Outlook 2010 kcients are installede by hand, they are all pushed to the client the same way, so they should behaive the same....

• Proposed as answer by Gary in Fresno Friday, September 17, 2010 5:49 PM

• Proposed as answer by Gary in Fresno Friday, September 17, 2010 5:49 PM

I recommend first trying the method that Ben M. Schoor suggests above using the Work Offline.  I had to wait several minutes after going to Work Offline before being able to delete the Stuck outbox message.  Besure to get out of Work Offline, back to Normal Outlook operaton.  Also, recommend deleting the problem stuck message from the Deleted Folder and closing Outlook 2010 and then reopen the Outlook 2010.

Trying to create a New Outlok Profile will lead you into problems unless you are very familiar with backing up you Outlook 2010 and reconfiguring all your email addresses, etc.  Doing this method you might as well remove Outlook 2010 which means removing Office 2010 suite.  Try to avoid this method of creating a New Outlook Profile for any version of Outlook.

• Proposed as answer by Gary in Fresno Friday, September 17, 2010 5:49 PM

I recommend first trying the method that Ben M. Schoor suggests above using the Work Offline.  I had to wait several minutes after going to Work Offline before being able to delete the Stuck outbox message.  Besure to get out of Work Offline, back to Normal Outlook operaton.  Also, recommend deleting the problem stuck message from the Deleted Folder and closing Outlook 2010 and then reopen the Outlook 2010.

Trying to create a New Outlok Profile will lead you into problems unless you are very familiar with backing up you Outlook 2010 and reconfiguring all your email addresses, etc.  Doing this method you might as well remove Outlook 2010 which means removing Office 2010 suite.  Try to avoid this method of creating a New Outlook Profile for any version of Outlook.

• Proposed as answer by Gary in Fresno Friday, September 17, 2010 5:49 PM

I  have the same problem...Outlook 2010 client but using Exchange 2003 on the back end.  Outbox slows to a crawl.  The best way I have found to resolve is to restart Outlook and the mail goes out right away.  I have recreated my profile with no difference.

Another problem I have is that getting Free Busy Info for meeting attendees is spotty...sometime it is immediate, sometimes takes forever, other times it never loads.

I recommend first trying the method that Ben M. Schoor suggests above using the Work Offline.  I had to wait several minutes after going to Work Offline before being able to delete the Stuck outbox message.  Besure to get out of Work Offline, back to Normal Outlook operaton.  Also, recommend deleting the problem stuck message from the Deleted Folder and closing Outlook 2010 and then reopen the Outlook 2010.

Trying to create a New Outlok Profile will lead you into problems unless you are very familiar with backing up you Outlook 2010 and reconfiguring all your email addresses, etc.  Doing this method you might as well remove Outlook 2010 which means removing Office 2010 suite.  Try to avoid this method of creating a New Outlook Profile for any version of Outlook.

I just want to add that I am experiencing this exact problem others are describing in this thread, with the main difference that I seldom send any large attachments so this happens even to tiny e-mails.

Normally everything works perfectly but then sometimes I can find there are e-mails waiting in the Outbox to be sent. These can be replies or "new" mails, doesn't matter. I am fully connected to Exchange when it happens and "All folders are up to date."If I do a Send / Receive All (F9) it just says Sending is "Completed".

I tried going into "Work Offline" to let the connections to Exchange disconnect. Then connected again, but this did in fact not help me. Sometimes I've been able to double-click the e-mail, press Send and it went away, but very seldom it works.

Safest way to get it back working is to exit Outlook and re-start. It's quite frustrating though when you send a quick reply, start working on something else and come back to discover your reply never went away.

I'm running Windows 7 64-bit with Outlook 2010 32-bit. I am connected to an Exchange 2007 server and freshly re-synced my complete profile a week ago to see if that could mitigate the problem, which it didn't.

Thankful for any assistance you might have in this matter!

Reply to Alex Jayson:

Only thing I can suggest is to open Outlook 2010 w/o connecting to the Exchange.  Then go into Work Offline with Outlook 2010, delete the messages stuck in the Outbox (you may have to wait a few minutes to do the delete just as I had to wait - why, I do not know), delete these messages from the Deleted foulder.  Close Outlook.  Shut down the PC and reboot.  Open Outlook and go back to Working Online.  Try sending a message with an attachment to besure Outlook 2010 has reset itself to normal operation. 

The other solution given to me was to remove Outlook 2010 or Office 2010 Suite; besure to backup Outlook first (the .pst Folders & Files) and deactivate Office 2010 if you need to remove Office 2010.  Hope you do not have to do this procedure as it is time consumming.

Best of luck.

• Proposed as answer by Gary in Fresno Friday, September 17, 2010 5:59 PM

Reply to Alex Jayson:

Only thing I can suggest is to open Outlook 2010 w/o connecting to the Exchange.  Then go into Work Offline with Outlook 2010, delete the messages stuck in the Outbox (you may have to wait a few minutes to do the delete just as I had to wait - why, I do not know), delete these messages from the Deleted foulder.  Close Outlook.  Shut down the PC and reboot.  Open Outlook and go back to Working Online.  Try sending a message with an attachment to besure Outlook 2010 has reset itself to normal operation. 

The other solution given to me was to remove Outlook 2010 or Office 2010 Suite; besure to backup Outlook first (the .pst Folders & Files) and deactivate Office 2010 if you need to remove Office 2010.  Hope you do not have to do this procedure as it is time consumming.

Best of luck.

• Proposed as answer by Gary in Fresno Friday, September 17, 2010 5:59 PM

Reply to Alex Jayson:

Only thing I can suggest is to open Outlook 2010 w/o connecting to the Exchange.  Then go into Work Offline with Outlook 2010, delete the messages stuck in the Outbox (you may have to wait a few minutes to do the delete just as I had to wait - why, I do not know), delete these messages from the Deleted foulder.  Close Outlook.  Shut down the PC and reboot.  Open Outlook and go back to Working Online.  Try sending a message with an attachment to besure Outlook 2010 has reset itself to normal operation. 

The other solution given to me was to remove Outlook 2010 or Office 2010 Suite; besure to backup Outlook first (the .pst Folders & Files) and deactivate Office 2010 if you need to remove Office 2010.  Hope you do not have to do this procedure as it is time consumming.

Best of luck.

In fact the message is not stuck such as that I cannot remove it, it is just stuck in the sense that it won't be sent away from the outbox, so I think our problems may be a little different.

Something I noticed today is that out of my two Exchange accounts this can happen just to one of them and as soon as I restart the application it is solved, but it is very very frustrating to be in a situation such as this.

Did you manage to sort out the issue? we have smiliar issue :

We have exchange 2007 running and the only user using outlook 2010 is having 'Disconnected from Exchange ' and 'trying to connect ' as status whenever he uses outlook outside the company network. He can receive emails smoothly but while sending emails, they tend to sit in outbox and go randomly after a restart of machine or the application. outlook 2010 within the domain is muh more stable then  whiel being used outside the network .

OS - Windows Vista 64 bit

Office - 2010 32 bit since the user heavily rely on Blackberry sync for contacts/calendar/tasks.

I have a message that is 38 MB that is stuck and it won't send and it won't delete.  When I try to open it, it says that it has already begun transmitting.  This suggestion didn't work.  Do you have any more suggestions?  Thanks.

I'm having the same problems. running Win7 Ultimate 64 bit Outlook 2010 32 bit

i've discovered work arounds but that is annoying. I recently was using 2007 on my laptop and didn't have these issues. I don't mind troubleshooting although for now i may just uninstall 2010. any fixes appreciated.

oh by the way...my emails have no attachments or pictures...all text.

I have the same problem but mine is using outlook 2010 and retrieving POP mail.  Reply messages are randomly getting stuck in the Outbox. 

My solution is to drag them to the Drafts folder and then resend from there.  Frustrating.

I have been dealing with this problem for some time. I work with executives and "workarounds" are not an option any longer. It makes me look bad because they think Microsoft wouldn't put out a product that doesn't work and "I" must be the one who is at fault.

I delete the profile and add it back in and everything works for a "while", then it may happen again randomly. The problem with this is that they may not notice that their outbox isn't sending emails and much of what they do is time sensitive. After I recreate their profile rarely am I able to resend the hung messages again and usually have to tell them to delete everything in the outbox and then recreate them. It's like the messages are corrupted and hang any subsequent emails from sending. This again is not met with cooperation...

I would rather not deploy any new software MS releases until there is at least the first service pack but the executives want the latest and greatest the day it comes out. I have searched the internet exhaustively for a solution, hotfix, trick to fix this that would be "invisible" to the user but have found none.

I am ready to open a ticket with MS but it would seem to me that if that was successful someone would have posted the results of that solution. I don't know why everyone here automaticly thinks of workarounds and the MS techs suggest workarounds when the software should just work and the responsiblity is on MS... I have a typical deployment Outlook 2010 on mostly XP & Win7 with an Exchange 2007 server. It's not anything that should raise issues...

If anyone has a fix or an invisible "reliable" workround I would appreciate the info. I would also like to encourage MS to send out a hotfix with this since I have experienced this issue with multiple clients in varying configurations so it's obviously a glitch. Other issues with Adobe add-ins and add-ins in general crashing out Outlook are annoying but since they involve different vendors I can accept the probability. Office 2010 is great but this one "little" problem is becoming a deal-breaker...

there are two issues. If you try to send an attachemnt that is to big it will get stuck. Go offline and you should be able to delete it.

the other issue which has carried over from outlook 2007 is that emails just stay in the outbox and do not send. You can move them into drafts or your inbox and open them and send them again but unfortunately for me and others it usually occurs when you do a mail merge (manually opening and sending 400 emails takes the efficiency out of things.

The send instantly fuctions works but sometimes i want to add  attachemnts to my mail merges so I want access befor i send/receive. (adding attachments seems to make the stuck email issue worse)

This is a pure outlook issue  - hope it gets fixed soon

The problem we are encountering is more general and more pervasive. We are using Outlook 2010 against Google Mail POP & SMTP servers (both generic gmail & Google Apps). 

Virutally all mail sent stays in the outbox for an indeterminate amount of time. We have tried all the solutions suggested in this thread prior to this date and none work. If we set "Send immediately" it still waits. We try send/receive - completes "successfully", but the mail is still in the outbox. We go offline, online, offline, online - still stuck. We set it to send/receive every 3 minutes - 20 minutes later it'll still be in the outbox. We turned off mail scanning on the anti-virus (AVAST!) - made no difference.

Eventually, all mail does get sent. Just not when we want it. It might be 10 minutes later or two hours later or something in-between. This is extremely frustrating, as you can imagine.

It has nothing to do with Exchange, as there is no Exchange in the equation here - only Outlook 2010 and SMTP.

It seems that some flag in Outlook is not getting set to make it actually process the outbox. Send/receive thinks it's doing its job, but it isn't.

The one thing we have not tried yet is the suggested freeware referenced by Alexey Kuznetsov on 12/10/2010 - I will research for reviews of it before attempting. If anyone has had good (or bad) experience with it - or any other solution, I'd appreciate hearing about it.

-Yosh

You can try to use this free tool:
http://www.outlookfreeware.com/en/products/all/OutlookMessagesU

• Proposed as answer by James Feldman Monday, September 09, 2013 4:25 AM

• Proposed as answer by James Feldman Monday, September 09, 2013 4:25 AM

Hello!

I had the same problem of messages that remained stuck in the Outbox of Outlook 2010 (32 and 64 bits) whenever I opened  the Outbox. 

The link below helped me solve my problem related to an Abbyy add-in that I disabled.

http://www.slipstick.com/problems/outbox.htm

hi!

Hi..

I also had similar problem mail stuck in outbox with deafult mail delivery set to PST on users with outlook 2010 and Exchange 2010.

I Installed the latest hotfix from Micorosoft. after that its working fine for our users..mails now not getting stuck in outbox..This hotfix not directly addressing this issue however it solved my problem..

Try to download this hotfix and apply in ur affected PC ...http://support.microsoft.com/kb/2475877

Regards

Thomas

Hi

I also get this sort of behaviour once in a while. When I try to close and open Outlook 2010 it does not seem to help. But if I restart Windows 7 (64) it seems to clear something up. As soon as I start Outlook after restart, all the e-mails are sent immediatly. Not an elegant solution but it works.

• Proposed as answer by MichaelBN Tuesday, May 31, 2011 2:47 AM
• Unproposed as answer by MichaelBN Tuesday, May 31, 2011 2:48 AM

• Proposed as answer by MichaelBN Tuesday, May 31, 2011 2:47 AM
• Unproposed as answer by MichaelBN Tuesday, May 31, 2011 2:48 AM

I’ve been struggling with this issue for some time. I finally noticed that the issue occurred with only certain email addresses on the exchange – If you delete all of your autocomplete entries and then re-add them it may solve your issue as it did for me.

Tried to apply the Hotfix mentioned above, but no resolution.

I noticed that the error 0x80040115 is associated with the stuck emails.  But there's little real help on the web with this.  Anyone have any further insight?

Hello, I despearately need some help. Using Outlook 2010.

None of those easy fix I read for the hundredth times has worked for the stuck email I have in my outbox. The offline option might work for some, but not for me.

I have tried using a new profile, even with the MDBVU32 process- which had worked for me on the Outlook 2003 version, but not with Outlook 2010 version.

The stuck email is large and it won't delete, it won't open, it won't cooperate with any of these steps. What else can I do?

I am still able to send new outgoing emails, but it has slowed down the outlook send and receive all together because Outlook keeps wanting to send this stuck email first.

Hello,

I had this problem.  I have just now realized that it is because of the companies logos etc included.  Go to Options > Mail > Replies, in the drop down choose "Do not include Original Message when replying" or something like that.

Seemed to have fixed it for me. 

Hope this helps you and others.

Regards

I've had a similar problem on many stations I recently upgrade to Office 2010 from Office 2007.  In every instance so far when someone has this problem I check their account settings and find two seperate Email accounts pointing to my Exchange server.  Once named default and the other named Microsoft Exchange.

Now if I go to File>Options>Advanced>Send/Receive and select All Accounts then the Edit button I show the default account which appears to not really be the default with a checked box for send/receive but the Microsoft Exchange account is unchecked.  If I change the checked boxes the problem is resolved and messages go out.

I also delete the default email account since it isn't the actual account used by users.  Please don't do this unless you are sure you're not actually deleting the account with all your email in it.

• Edited by xPenguinjasx Tuesday, September 06, 2011 8:45 PM

I've had a similar problem on many stations I recently upgrade to Office 2010 from Office 2007.  In every instance so far when someone has this problem I check their account settings and find two seperate Email accounts pointing to my Exchange server.  Once named default and the other named Microsoft Exchange.

Now if I go to File>Options>Advanced>Send/Receive and select All Accounts then the Edit button I show the default account which appears to not really be the default with a checked box for send/receive but the Microsoft Exchange account is unchecked.  If I change the checked boxes the problem is resolved and messages go out.

I also delete the default email account since it isn't the actual account used by users.  Please don't do this unless you are sure you're not actually deleting the account with all your email in it.

• Edited by xPenguinjasx Tuesday, September 06, 2011 8:45 PM

I've had a similar problem on many stations I recently upgrade to Office 2010 from Office 2007.  In every instance so far when someone has this problem I check their account settings and find two seperate Email accounts pointing to my Exchange server.  Once named default and the other named Microsoft Exchange.

Now if I go to File>Options>Advanced>Send/Receive and select All Accounts then the Edit button I show the default account which appears to not really be the default with a checked box for send/receive but the Microsoft Exchange account is unchecked.  If I change the checked boxes the problem is resolved and messages go out.

I also delete the default email account since it isn't the actual account used by users.  Please don't do this unless you are sure you're not actually deleting the account with all your email in it.

I'm seeing quite a lot of this happening as well and it's VERY hard to pin down.

Comment / observations:

@"xPenguinjasx"
"two seperate Email accounts pointing to my Exchange server"
> I pretty sure that scenario is already "acknowledged" by Microsoft and fixed in SP1
2285449 – Multiple Exchange accounts are created in Outlook 2001 when you have an existing Outlook profile after you install Office 2010.
http://support.microsoft.com/default.aspx?scid=kb;en-US;2285449

One a wider note - I'm obviously aware add-ins are seen as a possible cause
This is covered quite well here:
http://www.slipstick.com/problems/after-viewing-outlooks-outbox-the-messages-in-it-wont-send/

IMHO this area is far too diffiuclt to troubleshoot tho.
Identifying / rule-ing add-ins in / out via a process of elimination is VERY time consuming and not always conclusive in cases where this issue only happens very "sporadically".

If an add-in is "tocuching" a mail, ideally I want to be able to try "see" this via some sort of default log / debug output / util.
It dosn't seem possible right now (if anyone knows how to get a better insight into this please advise!)

IMHO Outlook logging needs to be dramatically improved (ideally completely overhauled because it's very poor)
It's far too "difficult" to pinpoint root cause when add-ins are invovled.
(if you do ask MS one of the first things you'll get told is to eliminate 3rd party addins, but in reality most people need those so want track down an issue with this in-place)

Microsoft also need to improve the "quality" of information on office fixes.
To demonstrate:
"Microsoft Office 2010 Service Pack 1 Changes.xlsx"
http://download.microsoft.com/download/5/1/2/512CC712-4070-4CFF-BC4A-B3AFF0E21A1E/Microsoft%20Office%202010%20Service%20Pack%201%20Changes.xlsx

Says "Messages get stuck in the Outbox"

Great - this sounds very relvent - but there is no KB article associated with this or link to additional info!
I should be able to click on a link which will tell me about the issue  / explain what was fixed and make a judgement if this is relevent

Lastly - the "sledgehammer" of re-creating mail profiles.
Often this is used / resorted to, but (IMHO) people "shouldnt have to do this".
Why are mail profiles primarily binary info / black box (apart from due to "legacy" reasons)
Why isn't this info in a more accessable form allowing issues to be properly troublshooted.

-AL

I have found disabling my antivirus program temporarily allows all stuck emails to be sent. I have had to do this with both Avast anti-virus and AVG anti-virus programs. I have had the same problem with Outlook 2007 and 2010. I don’t think it’s a Microsoft problem, just an overactive anti-virus program.

• Proposed as answer by dataportpc Monday, September 26, 2011 6:13 PM

I have found disabling my antivirus program temporarily allows all stuck emails to be sent. I have had to do this with both Avast anti-virus and AVG anti-virus programs. I have had the same problem with Outlook 2007 and 2010. I don’t think it’s a Microsoft problem, just an overactive anti-virus program.

• Proposed as answer by dataportpc Monday, September 26, 2011 6:13 PM

I have found disabling my antivirus program temporarily allows all stuck emails to be sent. I have had to do this with both Avast anti-virus and AVG anti-virus programs. I have had the same problem with Outlook 2007 and 2010. I don’t think it’s a Microsoft problem, just an overactive anti-virus program.

Turning off mail scanning in Avast did not work for me either, disabling the Avast program completely, allows me to send "stuck" mail instantly.

I have had this problem on Outlook 2007 and 2010, 32 bit and 64 bit Windows using Avast and AVG.

Try right button click on the message stuck in the outbox folder and select "forward". On the duplicate message that appears, press the send button. Press F9 to send/receive. Delete the stuck message from the outbox.

• Proposed as answer by aj_canada_81 Wednesday, September 28, 2011 5:23 PM
• Unproposed as answer by aj_canada_81 Wednesday, September 28, 2011 5:23 PM

Try right button click on the message stuck in the outbox folder and select "forward". On the duplicate message that appears, press the send button. Press F9 to send/receive. Delete the stuck message from the outbox.

• Proposed as answer by aj_canada_81 Wednesday, September 28, 2011 5:23 PM
• Unproposed as answer by aj_canada_81 Wednesday, September 28, 2011 5:23 PM

Try right button click on the message stuck in the outbox folder and select "forward". On the duplicate message that appears, press the send button. Press F9 to send/receive. Delete the stuck message from the outbox.

I have this issue (Outlook 2010) if I am disconnected from my Exchange server, send the message, then eventually connect expecting the Ooutbox to sync as other folders do.  Rather, messages sent while in offline mode remain stuck in the Outbox, even if Send/Receive is manually clicked.  It ironically claims that 'This folder is up to date'.  If I open up the message and click Send, still nothing happens.

To work around this, drag and drop the message(s) into another folder (i.e. Drafts) then from there open each message and click Send.  This re-places it into the Outbox but in this case it now actually sends (provided you are connected to your e-mail server).  FYI this only started happening after installing Outlook 2010 SP1.

I have messages stuck in outbox (Outlook 2010) with 2 Exchange accounts. (for the second account there are "send as" persmissions).

All works, but after a few days, messages start to get stuck with error 0X8004011D when I send mails from both accounts.

The strange thing is that the status bar for one account says: "Connected to Microsoft Exchange" and when I click on the other account it just says "Connected".

When I disable cached mode for both accounts, the status bar says for one account "Online with Microsoft Exchange" and the other one "Online". But then I can send mails for the main account. The other one keeps the messages stuck in the outbox, with no error at all.

Creating a new profile solves the issue for a few days and both accounts say "Connected to Microsoft Exchange". After a few days the same problems start over again.

I hope someone can figure this out. I already spend a lot of time on this issue. All updates are installed.

See previous approach above...

1. Move item from the Outbox to the Drafts folder
2. Open item from the Drafts folder
3. Click "Send"

Easy! Worked like a charm!

For the record, the problem as described in my post of Monday, February 21, 2011 1:04 PM still stands unsolved and unaddressed. We have tried ALL the suggested approaches here (including those posted after my original post, and that tool from Relief that I asked about) - and none have worked.

There is clearly some bug here. I hope someone from the Office team at MS takes note.

-Yosh

Agree with you - also have cases of this happening ongoing.

I've seen cases of:
- "mail stuck in outbox" - and not being sent
but also
- mail stuck in outbox" - but the mail actually does get sent !

I want to be able to pinpoint / troubleshoot the root cause(es) not ("just") have a way to re-send items which are stuck.

Fair enough Outlook is "extensible" (i.e. peopel can write add-isn for it), but it seems far too easy to "break" core functionality.

My "ideal" from a troubleshooting perspective would be:
  1) Have a way to flag / alert an item is "stuck" (e.g. noted in event log or a log file)
  2) Be able to turn on some sort of debug logging showing which add-ins are "touching" the items

-AL

I agree there has to be some way to troubleshoot and isolate the problem here - if someone knows how to do that, I'd like to know.

BTW, in the case I'm trying to solve there are NO add-ins, so this is core functionality that is broken without outside assistance... :-)

Once again, it's not that the mail stays stuck "forever" - it just doesn't get sent when it should, but rather some indeterminate amount of time later.

It's not as if this is a new issue. I remember when I had the same problem in Outlook 2003 - every once in a while mail would get stuck in the Outbox. I agree with yoshm, there is some core functionality that is broken and it has been for at least 8 years. Work arounds are just a way of patching over something that should not happen.

In the case I am dealing with, Outlook 2003 worked OK - mail was sent when it was supposed to be. The problem of send latency (i.e., getting stuck for an indeterminate amount of time in the outbox) only started after upgrading to Office 2010.

The bug may have existed earlier, but in my case, it only showed up after the upgrade.

I'm working with Outlook 2010 32-bit and Win 7 pro 32-bit connected to an Exchange 2007 server via RPC over HTTPS.  I can't even end the outlook.exe process after attempting to send an email.  It works fine until I go to send/receive and click "send all".  Yes, I have the option set to send them immediately.  It's a very simple message I'm sending with nothing but the word "test" in it with no signatures or attachments.

This was before and after installing Office 2010 SP1 and other Office updates.  I've recreated outlook profiles.  I've tested using pop instead of Exchange 2007 accounts.  I've disabled all addins.  I've uninstalled antivirus software (AVG that did NOT have the email protection portion installed from the beginning).  I've removed addins through the registry as suggested in a link in this thread.  I've renamed the sharing.xml.obi file.  I've ran repair installs on Office.  I've uninstalled and reinstalled Office and then updates before reconfiguring the outlook profile.  Nothing I've done has changed the behavior...  until now.

I logged on as a different user to the pc and connected to the external exchange server, sent mail, and all is working fine.  To anyone else reading this threadnaught, I suggest testing it through a different windows user profile, then renaming their windows profile, recreating, and moving data over.

But still, why does a thread have to go on for 8 months?   Please fix this, Microsoft.

• Edited by Fehz Tuesday, October 04, 2011 4:12 PM

I'm working with Outlook 2010 32-bit and Win 7 pro 32-bit connected to an Exchange 2007 server via RPC over HTTPS.  I can't even end the outlook.exe process after attempting to send an email.  It works fine until I go to send/receive and click "send all".  Yes, I have the option set to send them immediately.  It's a very simple message I'm sending with nothing but the word "test" in it with no signatures or attachments.

This was before and after installing Office 2010 SP1 and other Office updates.  I've recreated outlook profiles.  I've tested using pop instead of Exchange 2007 accounts.  I've disabled all addins.  I've uninstalled antivirus software (AVG that did NOT have the email protection portion installed from the beginning).  I've removed addins through the registry as suggested in a link in this thread.  I've renamed the sharing.xml.obi file.  I've ran repair installs on Office.  I've uninstalled and reinstalled Office and then updates before reconfiguring the outlook profile.  Nothing I've done has changed the behavior...  until now.

I logged on as a different user to the pc and connected to the external exchange server, sent mail, and all is working fine.  To anyone else reading this threadnaught, I suggest testing it through a different windows user profile, then renaming their windows profile, recreating, and moving data over.

But still, why does a thread have to go on for 8 months?   Please fix this, Microsoft.

• Edited by Fehz Tuesday, October 04, 2011 4:12 PM

I'm working with Outlook 2010 32-bit and Win 7 pro 32-bit connected to an Exchange 2007 server via RPC over HTTPS.  I can't even end the outlook.exe process after attempting to send an email.  It works fine until I go to send/receive and click "send all".  Yes, I have the option set to send them immediately.  It's a very simple message I'm sending with nothing but the word "test" in it with no signatures or attachments.

This was before and after installing Office 2010 SP1 and other Office updates.  I've recreated outlook profiles.  I've tested using pop instead of Exchange 2007 accounts.  I've disabled all addins.  I've uninstalled antivirus software (AVG that did NOT have the email protection portion installed from the beginning).  I've removed addins through the registry as suggested in a link in this thread.  I've renamed the sharing.xml.obi file.  I've ran repair installs on Office.  I've uninstalled and reinstalled Office and then updates before reconfiguring the outlook profile.  Nothing I've done has changed the behavior...  until now.

I logged on as a different user to the pc and connected to the external exchange server, sent mail, and all is working fine.  To anyone else reading this threadnaught, I suggest testing it through a different windows user profile, then renaming their windows profile, recreating, and moving data over.

But still, why does a thread have to go on for 8 months?   Please fix this, Microsoft.

We have Outlook 2010 on XP-Pro workstations with Exchange 2010 servers.

We have users here that have well over 10,000 items in their Sent Items folder and are still able to send emails while others which have much fewer items, have the stuck email issue, so the pst issue could not be the problem.

I have done some diagnostics to try to figure it out. In one particular case, the user sent an email at 9:35 am, she noticed that the email was stuck in the Outbox, then called the help desk. By the time I got the request the email had already gone, but I did a tracking of the message anyway to see if it showed anything. Our mailbox server never even showed the message as submitted from the client until 10:47am, more than an hour after it was sent by the user. Interestingly though, the same item in the users sent item folder showed it being sent at 9:35am, which is when the item first arrived in the user's Outbox.

With an Exchange account, the Outbox is located on the server along with all the other folders. In another case when I used a utility this see into the users Exchange account from a different workstation, the message that was stuck in the client's Outlook Outbox did not show up in the server outbox, so the Outlook client must be caching these messages. We do not have cached mode turned on either.

I have also noticed that when I initiate a send with the MAPI utility on the users workstation all messages on the client workstation that is affected will send.

The workaround that I have used with our clients is to have them use Outlook Web App. It does not have any issues with messages getting stuck in the Outbox. Most of our users don't like using it at the office though.

The disturbing fact here is this problem is growing, I have more and more users reporting the issue. Fortunately it is still a small percentage compared to the number of users I have. 350+

I hope this help in finding a resolution.

• Edited by Will-cap Friday, October 07, 2011 5:30 PM
• Proposed as answer by PGFarncombe Tuesday, October 18, 2011 2:29 PM

We have Outlook 2010 on XP-Pro workstations with Exchange 2010 servers.

We have users here that have well over 10,000 items in their Sent Items folder and are still able to send emails while others which have much fewer items, have the stuck email issue, so the pst issue could not be the problem.

I have done some diagnostics to try to figure it out. In one particular case, the user sent an email at 9:35 am, she noticed that the email was stuck in the Outbox, then called the help desk. By the time I got the request the email had already gone, but I did a tracking of the message anyway to see if it showed anything. Our mailbox server never even showed the message as submitted from the client until 10:47am, more than an hour after it was sent by the user. Interestingly though, the same item in the users sent item folder showed it being sent at 9:35am, which is when the item first arrived in the user's Outbox.

With an Exchange account, the Outbox is located on the server along with all the other folders. In another case when I used a utility this see into the users Exchange account from a different workstation, the message that was stuck in the client's Outlook Outbox did not show up in the server outbox, so the Outlook client must be caching these messages. We do not have cached mode turned on either.

I have also noticed that when I initiate a send with the MAPI utility on the users workstation all messages on the client workstation that is affected will send.

The workaround that I have used with our clients is to have them use Outlook Web App. It does not have any issues with messages getting stuck in the Outbox. Most of our users don't like using it at the office though.

The disturbing fact here is this problem is growing, I have more and more users reporting the issue. Fortunately it is still a small percentage compared to the number of users I have. 350+

I hope this help in finding a resolution.

• Edited by Will-cap Friday, October 07, 2011 5:30 PM
• Proposed as answer by PGFarncombe Tuesday, October 18, 2011 2:29 PM

We have Outlook 2010 on XP-Pro workstations with Exchange 2010 servers.

We have users here that have well over 10,000 items in their Sent Items folder and are still able to send emails while others which have much fewer items, have the stuck email issue, so the pst issue could not be the problem.

I have done some diagnostics to try to figure it out. In one particular case, the user sent an email at 9:35 am, she noticed that the email was stuck in the Outbox, then called the help desk. By the time I got the request the email had already gone, but I did a tracking of the message anyway to see if it showed anything. Our mailbox server never even showed the message as submitted from the client until 10:47am, more than an hour after it was sent by the user. Interestingly though, the same item in the users sent item folder showed it being sent at 9:35am, which is when the item first arrived in the user's Outbox.

With an Exchange account, the Outbox is located on the server along with all the other folders. In another case when I used a utility this see into the users Exchange account from a different workstation, the message that was stuck in the client's Outlook Outbox did not show up in the server outbox, so the Outlook client must be caching these messages. We do not have cached mode turned on either.

I have also noticed that when I initiate a send with the MAPI utility on the users workstation all messages on the client workstation that is affected will send.

The workaround that I have used with our clients is to have them use Outlook Web App. It does not have any issues with messages getting stuck in the Outbox. Most of our users don't like using it at the office though.

The disturbing fact here is this problem is growing, I have more and more users reporting the issue. Fortunately it is still a small percentage compared to the number of users I have. 350+

I hope this help in finding a resolution.

Hello Will-Cap

If you don't use pst's what do you use? That's your problem.

As your users have to sync so much information it is being triggered on send/receive.

There are no set limits for items, it has to do with tables in the file, I think there can be like 6090 entries per table per folder or something like that. People who send pdf attachments will be effected much more by this. I have seen users with over 13k items do just fine, and I have seen users with 7k items who have problems.

Using a PST is far better than other options and it keeps workers productive when they are not connected to the server.

The key to your problem is in your troubleshooting; mapi send works, so explicit send works, but send/receive does not. Check your sync logs and make sure av isn't scanning mail folders on the server. The send/receive details should provide a clue as to what is causing your sync delays.

Thanks

We are having the similar problems and here is the scenario:

Secretary has a somewhat large mailbox (2G), works for several attorneys and also has their huge mailboxes, the secretaries could have up to 4 other mailboxes

All users mailboxes are cached on a 2010 exchange server.

Outlook 2003 used to only cache the main users mailbox, Outlook 2010 caches all mailboxes, so now there is major synching trying to occur.  The secretaries are all having the same issues:

• They don't receive emails unless they click on Update Folders
• Their emails sit often sit in the Outbox
• They delete items that don't seem to go away
• They dismiss reminders that come back again

When I take them out of cache mode, everything returns to normal, but this is not an option. Our emergency email system relies on everyone being in cache mode.

When I remove the other user's mailboxes, everything returns to normal as well.

What we need is a way to only cache the users mailbox and not the attached mailboxes.  I have found a reg setting that is supposed to do this, but it doesn't seem to work

based on your details it sounds like the offline files have been corrupted. You need to close out outlook using file>exit and make sure it isn't running in the background.

Delete your offline files and open outlook again. Exchange will download a new copy of the information to outlook.

To prevent this from happening again, you will want to set up an archive policy. I never see these problems with a company who has a working archive policy and it is enforced on all folders. NEVER EVER.

Once the files are archived and you only have current email, you can right click the folder hive and goto properties and choose to compact the file. This will remove dead space and some fragmentation from the mail files as well.

Because you said it is relieved when disconnecting the others users mail file, that isolates the problem for you. See which mail file is causing the problem and run the scanpst after making a backup if you still have the issues after archiving.

There could be an old message in one of his folders either stuck or out of sync causing the problem.

Outlook can handle it, just has to be massaged from time to time. ;>

re: "What we need is a way to only cache the users mailbox and not the attached mailboxes"

> That is possible -  MS changed the default behaviour in OL2010 but it's easy to change it back as described in the MS KB article:

By default, shared mail folders are downloaded in Cached mode in Outlook 2010
http://support.microsoft.com/kb/982697

 HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\14.0\Outlook\Cached Mode
 Name: CacheOthersMail
 Type: DWORD:
 Value: 0

or via GPO as described in the article (assuming you actually want to enforce this)

-AL

re: "What we need is a way to only cache the users mailbox and not the attached mailboxes"

> That is possible -  MS changed the default behaviour in OL2010 but it's easy to change it back as described in the MS KB article:

By default, shared mail folders are downloaded in Cached mode in Outlook 2010
http://support.microsoft.com/kb/982697

 HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\14.0\Outlook\Cached Mode
 Name: CacheOthersMail
 Type: DWORD:
 Value: 0

or via GPO as described in the article (assuming you actually want to enforce this)

-AL

Hello Al,

I believe the user mentioned they tried that with no success. Also their emergency requirement would be circumvented if this is used. They need to fix the problematic mailbox. That user probably has a really crappy outlook experience but doesn't complain much about it.

Keep us posted!

I agree there has to be some way to troubleshoot and isolate the problem here - if someone knows how to do that, I'd like to know.

BTW, in the case I'm trying to solve there are NO add-ins, so this is core functionality that is broken without outside assistance... :-)

Once again, it's not that the mail stays stuck "forever" - it just doesn't get sent when it should, but rather some indeterminate amount of time later.

For the record - it's been over a year and no solution. The problem is still there. To review:

We are using Outlook 2010 against Google Mail POP & SMTP servers (both generic gmail & Google Apps). 

Virtually all mail sent stays in the outbox for an indeterminate amount of time. We have tried all the solutions suggested in this thread prior to this date and none work. If we set "Send immediately" it still waits. We try send/receive - completes "successfully", but the mail is still in the outbox. We go offline, online, offline, online - still stuck. We set it to send/receive every 3 minutes - 20 minutes later it'll still be in the outbox. We turned off mail scanning on the anti-virus (AVAST!) - made no difference.

Eventually, all mail does get sent. Just not when we want it. It might be 10 minutes later or two hours later or something in-between. This is extremely frustrating, as you can imagine.

It has nothing to do with Exchange, as there is no Exchange in the equation here - only Outlook 2010 and SMTP.

--

Hello!

I had the same problem of messages that remained stuck in the Outbox of Outlook 2010 (32 and 64 bits) whenever I opened  the Outbox. 

The link below helped me solve my problem related to an Abbyy add-in that I disabled.

http://www.slipstick.com/problems/outbox.htm

Hello,

   I have been searching for days on how to delete my outbox from trying to send an email. What happened was I sent a file over to another account not realizing the file was 108M! Now I can not delete it. Using the offline method, control panel method, I have been very unsuccessful.

   Also, when I updated to MS2010, my account is showing as a file, and outlook is the primary inbox. I am not able to utilize features like " find All" or "send to junk". I have tried creating the account again under POP 3, but only able to setup IMAP/SMTP.

Any help would be greatly appreciated.

Thank you in advance...

This is simple...once you know the trick. It isn't just 2010 but 2007 as well.

What you do is:

Shut down computer.

Disconnect modem.

Start up the computer and go to your e-mail.

Click on Outbox and highlight items in the box. 

Highlight and delete.

Shut down computer.

Hook up modem..

Once up, you'll be up and running again with no delays and Outbox will be empty.

I have this problem with pictures/videos. When we try to send more than 3 or even 4 pictures, and all videos, they get stuck in outbox and you need to repeat the above to empty it.

After two hours of dealing with this issue and trying almost everything in this thread, I found a solution that worked instantly.

The fix is actually very simple: I decreased the MTU value in my router from 1500 to 1400 and my emails stuck in Outbox were sent immediately.

This means Outlook was trying to communicate with my SMTP server using the default packet size available in Windows (1500), but for some unexplicable reason (my DSL provider tweaking their network or what), the SMTP server was not able to accept them.

Decreasing MTU to a lower value was an instant fix in my case, give it a shot if nothing else works...

• Proposed as answer by Kevin Lyon MITI Wednesday, October 30, 2013 6:38 AM

After two hours of dealing with this issue and trying almost everything in this thread, I found a solution that worked instantly.

The fix is actually very simple: I decreased the MTU value in my router from 1500 to 1400 and my emails stuck in Outbox were sent immediately.

This means Outlook was trying to communicate with my SMTP server using the default packet size available in Windows (1500), but for some unexplicable reason (my DSL provider tweaking their network or what), the SMTP server was not able to accept them.

Decreasing MTU to a lower value was an instant fix in my case, give it a shot if nothing else works...

• Proposed as answer by Kevin Lyon MITI Wednesday, October 30, 2013 6:38 AM

After two hours of dealing with this issue and trying almost everything in this thread, I found a solution that worked instantly.

The fix is actually very simple: I decreased the MTU value in my router from 1500 to 1400 and my emails stuck in Outbox were sent immediately.

This means Outlook was trying to communicate with my SMTP server using the default packet size available in Windows (1500), but for some unexplicable reason (my DSL provider tweaking their network or what), the SMTP server was not able to accept them.

Decreasing MTU to a lower value was an instant fix in my case, give it a shot if nothing else works...

Wayne paul, does your solution, send the stuck emails after you do the above?  i understand it deletes the outbox but does it send the stuff stuck in outbox? 

Am I understanding correctly, that after you send the picture or video it actually sends but the outbox holds it?  I want to make sure when I send something that it sends...  Please explain

mary

jazzy joe,  what is MTU and where do i go to change this....

mary

I tried #2 and still have the problem. I also did the following, all withe the problem still there:

1. Uninstall and reinstall Office 2010 Professional Plus

2. Turn off anti0virus outgoing email scan

3. Empty the sent box

4. Run System Mechanic Pro as well as PC Matic, a full system scan with Norton Internet Security 2012 and defraggler

5. Search the web

Nothing seems to help. I am ready to use a different email program.

I have the same issue which started only recently, I have 3 other email addresses on the same domain which all work correctly so I am leaning towards the size of the file/folders in the problem email address.  Can anyone give any advice on maximum file sizes ?

To remove a blocked email from outbox the simplest method is to drag to 'draft' folder open and resend

Hi Guys,

I had the same problem, outlook2010, exchange2010.

mails that i send and then edit in the outbox folder will not be sent ! (they are now stuck in the outbox folder with date=none

the solution was to play with the outlook add ins.

i found that Symantec Endpoint Protection (antivirus) outlook add ins caused my problem.

i had disabled it, restarted outlook, and my problem is now solved !

i can now edit mails in the outbox folder and they will be sent as they should !

good luck !

Tomer Shoshan.

• Proposed as answer by wouterpinkhof Friday, May 04, 2012 10:01 AM

Hi Guys,

I had the same problem, outlook2010, exchange2010.

mails that i send and then edit in the outbox folder will not be sent ! (they are now stuck in the outbox folder with date=none

the solution was to play with the outlook add ins.

i found that Symantec Endpoint Protection (antivirus) outlook add ins caused my problem.

i had disabled it, restarted outlook, and my problem is now solved !

i can now edit mails in the outbox folder and they will be sent as they should !

good luck !

Tomer Shoshan.

• Proposed as answer by wouterpinkhof Friday, May 04, 2012 10:01 AM

Hi Guys,

I had the same problem, outlook2010, exchange2010.

mails that i send and then edit in the outbox folder will not be sent ! (they are now stuck in the outbox folder with date=none

the solution was to play with the outlook add ins.

i found that Symantec Endpoint Protection (antivirus) outlook add ins caused my problem.

i had disabled it, restarted outlook, and my problem is now solved !

i can now edit mails in the outbox folder and they will be sent as they should !

good luck !

Tomer Shoshan.

Here is my issue:

Outlook 2010 /Exchange 2010 online mode ( cache mode is disable by GPO)

I sent some email using  "Delayed" Options. Those email are supposed to send out after a specified date in the future and it didn't.

I followed the the instruction provided by Tomerikko and realized that the Symantec Endpoint Protection (SEP) Outlook Add in is "checked"

Unchecked the SEP and it works.

I will have to file a ticket with Symantec since this is a feature and is supposed to work.

Thanks all

Are you running an older SEP build in your environment? Make sure you are running the latest (11.0.7200.1147), some older versions did have reported issues with Outlook. You can download RU7 MP2 from Fileconnect with a valid serial number.

https://fileconnect.symantec.com/licenselogin.jsp?localeStr=en_US

I have a variant on this problem.  

If there is an attachment while using VPN and you send the e-mail and it goes into the Outbox. If you go to the outbox and hit Send/Receive it might go out if you are fast enough (I used the same message and attachments with immediate response and delayed response -- if you delay the problem is manifest).  If you open the message and hit Send there is no action, the progress of Send/Receive is shown and it shows no errors but the message is still there.  Open the message and it says along the top that the Message will not send automatically, it has acquired a delayed delivery attribute, check the options and message is set not to go till the end of the day, uncheck the delay option, save (or don't save) click the send button the message closes, Send/Receive, message is still there.  Open the message and the delay option is still on.  I tried changing the time for send to some time in the past, i.e. 10:00 am and it was 11:30 am.  Send/Receive.  Nothing.  Wait 10 min. (Set option send receive every 2 min and saw the process go but message is stuck).  Did research.  Set Off-line mode, went back on-line with out effect.  I repeated waiting longer -- 10 min. -- and went back on-line waited 10 min and I saw 3 of the Send/Receive processes but still the message sat in the Outbox.  Logged off the VPN, shut down the computer, brought the computer into the office and connected to the lan repeat all of the above and still no sending that message.  Nothing seemed to work and connecting to the network did not resolve it. Messages came in on the VPN and the LAN and other messages went out on the LAN -- did not try to invoke other short e-mails when I was on the VPN.  I even deleted the srs file thinking something might be wrong with it.....

A poor work-around was found from others in this thread, drag the e-mail into the drafts, open the e-mail and then send.  Voila.  A poor voila but a voila all the same.

Ben Schorr's suggestion works: 

"Click Send/Receive | Work Offline.  Go to the Outbox and delete the stuck messages.  Click Send/Receive and Work Offline again."

At first I couldn't find the "Work Offline" because I was simply clicking on the Send/Receive icon that appears to far right when I was on the "Home" tab at top of Outlook.

But then I saw the Send/Receive tab just to the right of the "Home" tab at top. When I clicked on it, then I could see the "Work Offline" icon to the far right, which toggles off and on.

It still didn't work until I let "Work Offline" sit for a long time (overnight, but perhaps that was overkill) and this morning I deleted the stuck message with no problem!

Thank you, Ben Schorr, for solving the problem!

I've think I found a simple workaround to this problem for Outlook 2010.  Go to the Options panel, then the Advanced option and check the box that says "SEND IMMEDIATELY WHEN CONNECTED" in the Send/Receive option.  I tested this and it worked GREAT.  No more problem of emails getting stuck in the OUT folder with a "DATE: NONE".  If you can live with your emails being sent immediately when clicking send, this is the perfect solution to this prob

Account Settings

More Settings

Outgoing Server Tab

Uncheck "My outgoing server (SMTP) requires authentication"

My ISP also had me click on the Advanced Tab and change my Outgoing server (SMTP) port to 587

• Edited by Jim Nolan 24 Thursday, June 14, 2012 11:18 PM
• Proposed as answer by Jim Nolan 24 Thursday, June 14, 2012 11:18 PM

• Edited by Jim Nolan 24 Thursday, June 14, 2012 11:18 PM
• Proposed as answer by Jim Nolan 24 Thursday, June 14, 2012 11:18 PM

You can also go File open Advanced Send Receive Setting for group "All Accounts" Tick schedule an automatic send/receive every 30min tick this option and change to 2 min. 

This has helped in our corporate environment just going to MS Office 2010 (Servers: Exchange 2007, Desktop: Windows XP SP3).

The default install doesn't have that option ticked. We tick the options and issue goes away.  

Thank you for the reply, 

Yeah I check with our Mail engineer techs they advised that option is enabled. This is happening to random users and at random times. The current workaround is on the desktop side Tick Schedule Send/Recieve change from 30min to 2min. Also on the Exchange side profile the users account and set that option. The issue goes away.

This is happening for MS Office 2007/2010 users. 

Could there be a network issue in our environment?

The best way to get rid of this problem is following the following steps;

Click on start>type scanpst.exe>run the file scanpst.exe>Browse for Outlook.pst file>Click start>Repair.

Restart Outlook again. If you still see the msgs in your outbok. You can move it to sent folder. Try and send a new msgs your problem should be fixed by now :)

• Edited by Prab007 Saturday, August 11, 2012 10:31 AM

The best way to get rid of this problem is following the following steps;

Click on start>type scanpst.exe>run the file scanpst.exe>Browse for Outlook.pst file>Click start>Repair.

Restart Outlook again. If you still see the msgs in your outbok. You can move it to sent folder. Try and send a new msgs your problem should be fixed by now :)

• Edited by Prab007 Saturday, August 11, 2012 10:31 AM

The best way to get rid of this problem is following the following steps;

Click on start>type scanpst.exe>run the file scanpst.exe>Browse for Outlook.pst file>Click start>Repair.

Restart Outlook again. If you still see the msgs in your outbok. You can move it to sent folder. Try and send a new msgs your problem should be fixed by now :)

The only success I have had is to delete the mail profile.

Before deleting the mail profile, move the content of the Outbox into a new folder you create within the Inbox or the contents may be lost.

Close Outook

Control Panel>Mail> Delete existing profile.
Add new profile, reopen Outlook, move all of the Outbox contents back into the Oubox folder. You will then have to open each individual email within the Outbox and click "Send".

Delete the folder you created within the Inbox to temporarily store your Outbox items.

navigate to account settings

second tab (datafiles or something like this)

click on file storage location

then delete all .pst files

Takes about 30 seconds and your stuck mails are gone

If you use POP3, your mails will probably be lost. If you use IMAP, Outlook will simply sinc with the server again and create new .pst files!

Is there any update to this issue?

We have Outlook 2010 and some users suddenly cant send email. They get stuck in outbox. All users work online ( non cached) and the only "solution" (workaround) is to recreate the Outlook profile.

When the issue occure they get an error on send\receive with something with not having accessrights to complete this operation (access denied).

Is this a Bug in Outlook 2010 and is there a permanent sollution so we dont have to recreate these Outlook profiles?

• Edited by Huguinho_StaCatarina Tuesday, August 28, 2012 8:28 PM

• Edited by Huguinho_StaCatarina Tuesday, August 28, 2012 8:28 PM

Can you please tell me how to connect & disconnect from the domain?

Thanks

Fix for this is to simply ensure you unplug network connectivity to your machine laptop or desktop no link to internet:)  One step more than simply clicking working off line:) 

Then simply delete the message in the outbox this worked right away after all the other solutions failed.  It appears that the send feature keeps trying to send the e-mail thus blocking the delete command/move command or any other system requests. 

The Message I kept receiving was the it was being transmitted. 

So once I stopped the network connectivity the E-mail message was not actively trying to be sent and I was able to delete it:) Hope this helps  The Ronin

• Edited by The True Ronin Friday, September 28, 2012 9:03 PM

Fix for this is to simply ensure you unplug network connectivity to your machine laptop or desktop no link to internet:)  One step more than simply clicking working off line:) 

Then simply delete the message in the outbox this worked right away after all the other solutions failed.  It appears that the send feature keeps trying to send the e-mail thus blocking the delete command/move command or any other system requests. 

The Message I kept receiving was the it was being transmitted. 

So once I stopped the network connectivity the E-mail message was not actively trying to be sent and I was able to delete it:) Hope this helps  The Ronin

• Edited by The True Ronin Friday, September 28, 2012 9:03 PM

Fix for this is to simply ensure you unplug network connectivity to your machine laptop or desktop no link to internet:)  One step more than simply clicking working off line:) 

Then simply delete the message in the outbox this worked right away after all the other solutions failed.  It appears that the send feature keeps trying to send the e-mail thus blocking the delete command/move command or any other system requests. 

The Message I kept receiving was the it was being transmitted. 

So once I stopped the network connectivity the E-mail message was not actively trying to be sent and I was able to delete it:) Hope this helps  The Ronin

Hi Moon,

I had this problem at work for ages, but we have found a fix that has worked everytime (with an Exchange server).

The following was our solution:

1.  Right click the email address that is giving you problems.

2.  Choose outlook properties - its on the last drop down box of the address card.

3.  The third option down on our system is email type: (it may say mailto (hopefully) in the box - if so click the box next to it on the right.

4.  Reopen the message and click send.

HTH

Paul

• Edited by highburycottage Tuesday, October 02, 2012 8:05 AM

Hi Moon,

I had this problem at work for ages, but we have found a fix that has worked everytime (with an Exchange server).

The following was our solution:

1.  Right click the email address that is giving you problems.

2.  Choose outlook properties - its on the last drop down box of the address card.

3.  The third option down on our system is email type: (it may say mailto (hopefully) in the box - if so click the box next to it on the right.

4.  Reopen the message and click send.

HTH

Paul

• Edited by highburycottage Tuesday, October 02, 2012 8:05 AM

Hi Moon,

I had this problem at work for ages, but we have found a fix that has worked everytime (with an Exchange server).

The following was our solution:

1.  Right click the email address that is giving you problems.

2.  Choose outlook properties - its on the last drop down box of the address card.

3.  The third option down on our system is email type: (it may say mailto (hopefully) in the box - if so click the box next to it on the right.

4.  Reopen the message and click send.

HTH

Paul

I have been experiencing the "stuck in the outbox" issue for some time on a stand-alone pc with Outlook 2010.  I have tried creating a new profile, repairing the .pst files, even the OLFix solution (which just corrupted my profile and forced me to create a new one in order to get Outlook working again).  None of these solutions have worked.

I have several POP3 and IMAP accounts set up in my Outlook.  The default account is POP3.  My outlook is set up with send/receive set to manual.

There are a few things that I have noticed, however, and was wondering if others have seen the same and if my experience will provide any further clues to this problem:

If I send an email from any account, then check the outbox, the email is there but it is not italicized as normal and is listed under "Date: None"  There is no problem deleting the email; however, if I leave it in the outbox and create/send another email, it goes into the outbox under "Date: Today", is italicized, and sends OK.  If I left or right click on the good email before sending, it changes to non-italicized and moves itself into the "Date: None" category and stays there until deleted.

As Arte Johnson used to say (on Laugh-In), "Very Interesting."

Yes, they actually do send if I don't look at them.  That would also explain why sometimes (while looking at the outbox as I click "send" on the email compose screen) I have seen it appear italicized for a fraction of a second, then change to non-italicized (probably the instances of this that I witnessed was for a large email which took the offender a fraction of a second to "read".

Thanks a bunch Diane (I'll stop looking . . . I promise.  :)

Works Perfect

Many Thanks to you

This may be too late to be of any good to anyone, but I have been having this problem intermittently. What fixed it was following these instructions found on this page:

I had 7 mails stuck in the outbox after getting under my message quota.  4 sent when I clicked Send/Receive, 3 remained stuck.  I Ran Unstuck Email from ReliefJet Essentials and it said it found no trouble and the mail remained.

I then tried right-clicking each email and chose Reply/All... it oppened an email that looked just like my original, addressed and dated with the current time, but they sent properly!

THANK YOU GARY!!

Your solution WORKED!!

I clicked "work offline", exited Outlook, opened Outlook back up as "work offline"

I was then able to DELETE the outgoing email that was hung up!!

A thousand THANK YOU's!!! :0)

• Proposed as answer by Linda in Auburn, CA Friday, December 07, 2012 3:32 PM

THANK YOU GARY!!

Your solution WORKED!!

I clicked "work offline", exited Outlook, opened Outlook back up as "work offline"

I was then able to DELETE the outgoing email that was hung up!!

A thousand THANK YOU's!!! :0)

• Proposed as answer by Linda in Auburn, CA Friday, December 07, 2012 3:32 PM

THANK YOU GARY!!

Your solution WORKED!!

I clicked "work offline", exited Outlook, opened Outlook back up as "work offline"

I was then able to DELETE the outgoing email that was hung up!!

A thousand THANK YOU's!!! :0)

Thanks for the links roger, I've been struggling with this problem for months.

My emails would not send because they would immediately switch to the "Read" status (as opposed to "Unread" status) -- Outlook won't send emails in "read" status.  Turns out my problem was caused by the Apple iCloud and Change Notifier add-ins.  My solution was to disable those add-ins and close and restart Outlook.  After that, my emails stay in the "unread" status in the Outbox until I press "Send All" from the "Send / Receive" ribbon tab.  (note: I have "Send immediately when connected" UNchecked ... File > Options > Advanced tab > Send and receive section > "Set send and receive settings for incoming and outgoing items.")

Another work-a-round is to open Outlook in safe mode (which disables most add-ins) and send in that state.  After sending emails, close out of safe mode and re-open Outlook in regular mode.

Ref:

http://www.slipstick.com/problems/after-viewing-outlooks-outbox-the-messages-in-it-wont-send

http://www.slipstick.com/problems/outlook-and-icloud-2-what-you-need-to-know/

• Proposed as answer by Kevin Pitkin Friday, May 31, 2013 1:39 PM

Thanks for the links roger, I've been struggling with this problem for months.

My emails would not send because they would immediately switch to the "Read" status (as opposed to "Unread" status) -- Outlook won't send emails in "read" status.  Turns out my problem was caused by the Apple iCloud and Change Notifier add-ins.  My solution was to disable those add-ins and close and restart Outlook.  After that, my emails stay in the "unread" status in the Outbox until I press "Send All" from the "Send / Receive" ribbon tab.  (note: I have "Send immediately when connected" UNchecked ... File > Options > Advanced tab > Send and receive section > "Set send and receive settings for incoming and outgoing items.")

Another work-a-round is to open Outlook in safe mode (which disables most add-ins) and send in that state.  After sending emails, close out of safe mode and re-open Outlook in regular mode.

Ref:

http://www.slipstick.com/problems/after-viewing-outlooks-outbox-the-messages-in-it-wont-send

http://www.slipstick.com/problems/outlook-and-icloud-2-what-you-need-to-know/

• Proposed as answer by Kevin Pitkin Friday, May 31, 2013 1:39 PM

Thanks for the links roger, I've been struggling with this problem for months.

My emails would not send because they would immediately switch to the "Read" status (as opposed to "Unread" status) -- Outlook won't send emails in "read" status.  Turns out my problem was caused by the Apple iCloud and Change Notifier add-ins.  My solution was to disable those add-ins and close and restart Outlook.  After that, my emails stay in the "unread" status in the Outbox until I press "Send All" from the "Send / Receive" ribbon tab.  (note: I have "Send immediately when connected" UNchecked ... File > Options > Advanced tab > Send and receive section > "Set send and receive settings for incoming and outgoing items.")

Another work-a-round is to open Outlook in safe mode (which disables most add-ins) and send in that state.  After sending emails, close out of safe mode and re-open Outlook in regular mode.

Ref:

http://www.slipstick.com/problems/after-viewing-outlooks-outbox-the-messages-in-it-wont-send

http://www.slipstick.com/problems/outlook-and-icloud-2-what-you-need-to-know/

I just recently started experiencing the issue yesterday, then had the same thing happen today. Yesterday, I solved the issue when I noticed that the email in question was actually open. Once I closed the message and hit F9 (Send and Receive) the message sent. So, this morning, when I had the same thing occur, I checked to see if the email message was open. I did not initially see it in the running task bar so I became suspicious. After about 10 minutes it mystically appeared.

Is it possible that I overlooked this, doubtful on account of recent experience. I would say the first thing you should try here is to close Outlook, then reopen it and try to manually Send/Receive.

As with any issue, always start with the simple stuff...hope this helps!

Happy New Year,

Eric

I've used Outlook 2010 for two years without ANY trouble. One morning I sent an e-mail that went out as usual, follwed immediately by another that got stuck in the outbox.  It never occurred to me that my problem might be the outgoing server (SMTP) port.  I missed it in all these posts, but found a reference to it in Leo Notenboom's website.   After reading about port 25 prohibitions I went to the Comcast website and did some research--they've discontinued use of port 25 for outgoing e-mail.  (Was that discontinued between my two e-mails?...)  They had a fairly good "how to" that I followed and viola, I'm back in business.

I have just seen this happening for a client where we have noticed that it is only happening to the users connected over VPN and only to users connecting to the legacy Cisco VPN but not happening to the new Juniper VPN they have implemented.

I investigated a bit further and changed Outlook from using RPC connection to HTTPS by selecting the check boxes to connect using HTTP first on both slow and fast networks. This fixed the problem.

However, I only see this as a workaround and not as a solution to the underlying problem. I feel the underlying problem is related to connectivity / networking as the RPC connections works OK over the Juniper VPN and when users are on the corporate WAN. However, I currently do not a way to prove it or to know what needs fixing. I haven't done any latency or jitter testing yet. I wonder if anyone is able to give any pointers?

Thanks

Nauman.

I am having an issue with this here at work.  This is going to be lengthy, but maybe someone can help me out.

We have a group of users that have a department mailbox along with their personal mailbox in the Navigation Pane.  Both mailboxes (on Exchange 2007) are set up as two accounts (go to File tab > Account Settings > Account Settings... and you see them both). 

Messages started getting stuck in the Outbox about 4months ago and I am not sure how to solve this.  Here is what I did to troubleshoot the issue. 

• I removed the mailboxes and re-added them and that worked for a little bit, but the same issue came back.
• I tested it out in OWA and the message is still stuck (verifying it's not the Outlook install on the PC)
• Sent out multiple test messages and not a single one gets stuck in the Outbox.
• Moved the mailbox to a different store, didn't fix the issue.
• Verified that no one is editing the e-mails when they're in the Outbox.  Users are leaving it alone as is.
• The e-mails only contain text.  None of the messages had attachments or any kind of images at all.
• Set up separate profiles (Start > Control Panel > Mail) and tested it out that way.
• Switching to Cached Mode makes the message disappear, but as soon as you revert back you still see it (I don't consider this a solution).

If anyone can assist with this or give me any kind of ideas that would be great.  I'm looking to resolve this issue and get it fixed once and for all!

I bit the bullet and recreate my profile.  (THIS IS ALL ON POP) and used the same PST as before and now my messages do send normal.  there has to be a bug in outlook 2010.

The folder needs to synchronise. This has also happened to me. In a nutshell, what happened is that I did a send/receive and logged off about 2 to 3 minutes later. The article that I'll link to says that it can take up to 30 minutes to synchronise, so when I log off 2 or 3 minutes after sending the synchronisation has not completed. Technet is not allowing me to add the link here, but just search for kb 842284 in lieu of a link.

The KB article describes manual synchronisation. What worked for me was going back onto the computer I sent mail from, I opened a few emails and then when I saw the message at the bottom that said it was synchronising I then logged off and the messages showed as sent.

Hi,

I have been working with this issue for 3 days and have found a solution.

We had the same issue where only our 2010 clients had problem with emails not leaving the out box. We are running exchange 2007.

All we did to resolve the issue is Installed Rollup 13 update for Exchange 2007 SP3 on the server and rebuilt the Client Access Services on IIS

After that we restarted the clients outlook and now no more problems

I hope this helps

I agree. 

Here's my workaround which has so far worked every time:

Am not on exchange server, and the problem is NOTonly for emails with attachments.  Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

:(

Am not on exchange server, and the problem is not only for emails with attachments.  Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

:(

Am not on exchange server, and the problem is not only for emails with attachments.  Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

:(

That only sometimes works. Here's my workaround:

Am not on exchange server, and the problem is not only for emails with attachments.  Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) Transfer the stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

:(

Not perfect because not everyone wants their emails sent immediately. But, then my solution is only a workaround too. This is a many years' long problem of Microsoft which THEY should address and fix, period.

Am not on exchange server, and the problem is not only for emails with attachments.  Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email.

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

:(

Only workaround I have tried/seen to date that works is:

Am not on exchange server, and the problem is not only for emails with attachments.  Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) transfer the stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email. (You can resend them all at once, but I've done one at a time until I know it's working.)

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

:(

Am not on exchange server, and the problem is not only for emails with attachments. Nor is it only for reply emails, but for originated new emails as well.  Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) Transfer the stuck emails to Drafts.

2) Reboot the computer.

3) Transfer and send each stuck email. (You can resend them all at once, but I've done one at a time until I know it's working.)

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

:(

Am not on exchange server, and the problem is not only for emails with attachments. Nor is it only for reply emails, but for originated new emails as well.  Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) Transfer the stuck emails to Drafts. (Just as a safeguard so as not to lose them.)

2) Reboot the computer.

3) Transfer and send each stuck email. (You can resend them all at once, but I've done one at a time until I know it's working.)

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

:(

Am not on exchange server, and the problem is not only for emails with attachments. Nor is it only for reply emails, but for originated new emails as well.  Have had Outlook 2010, with my new computer bought last November, only a year and this problem just began in the last month. (Used to have the problem from time to time in 2003 as well.)

My fixes (not ideal as Microsoft has known of the problem for years and just hasn't bothered to fix it) are

1) Transfer the stuck emails to Drafts. (Just as a safeguard so as not to lose them.)

2) Reboot the computer.

3) Transfer and send each stuck email. (You can resend them all at once, but I've done one at a time until I know it's working.)

4) Wait for the problem to turn up again in a couple weeks as it most surely will!

:(

Hi all

I run win 7 Ultimate 64 bit and Office Pro Plus 2010.

I have recently developed the same problem with outlook 2010..

I have office pro plus 2010 and I have been using it since mid 2011 without any problems at all, in particular as the one described above.

About a week or so ago I noticed my emails were getting moved to the outbox instead of being sent directly as was the case in the past. I know that I have made NO changes whats so ever to my outlook configuration.

EXCEPT FOR ONE THING !!  I recently downloaded and installed Norton 360 30 day trial.. 

I have just removed the 360 trial and cleaned out the directories of all references and restarted my computer, opened outlook and tested a number of emails i had trouble with and they all worked as before...

No Norton 360 and outlook works fine.. All messages are sent immediately, as before.

I am going to re install my previous internet security suite and test it for a week and post the results for you.

This may or may not be of any help you you but thus far my outlook is functioning as per normal. 

• Proposed as answer by TheAxe77 Saturday, January 18, 2014 1:33 AM

Hi all

I run win 7 Ultimate 64 bit and Office Pro Plus 2010.

I have recently developed the same problem with outlook 2010..

I have office pro plus 2010 and I have been using it since mid 2011 without any problems at all, in particular as the one described above.

About a week or so ago I noticed my emails were getting moved to the outbox instead of being sent directly as was the case in the past. I know that I have made NO changes whats so ever to my outlook configuration.

EXCEPT FOR ONE THING !!  I recently downloaded and installed Norton 360 30 day trial.. 

I have just removed the 360 trial and cleaned out the directories of all references and restarted my computer, opened outlook and tested a number of emails i had trouble with and they all worked as before...

No Norton 360 and outlook works fine.. All messages are sent immediately, as before.

I am going to re install my previous internet security suite and test it for a week and post the results for you.

This may or may not be of any help you you but thus far my outlook is functioning as per normal. 

• Proposed as answer by TheAxe77 Saturday, January 18, 2014 1:33 AM

OK, I've JUST FIXED THIS ISSUE on my PC - this may or may not work for you. 

I am running Win7 - Outlook 2010 - Norton 360

Solution:
Open Norton 360
Settings > AntiSpam > Turn it OFF!

I restarted outlook, unfortunately the mails that were stuck with "Date:None" remained, so I deleted these and tried re-sending my emails again as new mails and they sent straight away (momentarily passing through outbox).  

I now have instant Sending happening when  I compose a mail message

My thoughts on this are; Norton uses 'Protected ports' 25 and 110 - however, my mail server uses different incoming and outgoing ports and I was unable to add these as protected ports in Norton getting a message similar to "These ports are in use by another program and cannot be protected".  I believe that Norton AntiSpam is blocking mail on any port it isn't capable of protecting.  I assume if I was using ports 25 and 110 that it would work (though I haven't tried this).  

Hope this helps!

• Proposed as answer by TheAxe77 Saturday, January 18, 2014 1:42 AM

OK, I've JUST FIXED THIS ISSUE on my PC - this may or may not work for you. 

I am running Win7 - Outlook 2010 - Norton 360

Solution:
Open Norton 360
Settings > AntiSpam > Turn it OFF!

I restarted outlook, unfortunately the mails that were stuck with "Date:None" remained, so I deleted these and tried re-sending my emails again as new mails and they sent straight away (momentarily passing through outbox).  

I now have instant Sending happening when  I compose a mail message

My thoughts on this are; Norton uses 'Protected ports' 25 and 110 - however, my mail server uses different incoming and outgoing ports and I was unable to add these as protected ports in Norton getting a message similar to "These ports are in use by another program and cannot be protected".  I believe that Norton AntiSpam is blocking mail on any port it isn't capable of protecting.  I assume if I was using ports 25 and 110 that it would work (though I haven't tried this).  

Hope this helps!

• Proposed as answer by TheAxe77 Saturday, January 18, 2014 1:42 AM

• Edited by jimmyjackjoe Saturday, April 05, 2014 1:18 PM

• Edited by jimmyjackjoe Saturday, April 05, 2014 1:18 PM

I understand this is a very dated post but I wanted to offer my two bits.  Most recently I had a situation where my Outlook 2010 would have messages stuck in the outbox. All the advice given is solid but I would add one more thing. After performing all the recommended procedures (including deleting and recreating the outlook profile) I finally deleted the old Outlook profile folder. Actually, I renamed it. So, perform the following:

1. In outlook, click FILE, ACCOUNT SETTINGS dropdown box, ACCOUNT SETTINGS
2. Click DATA FILES tab
3. Click OPEN FILES LOCATION
4 Exit Outlook

In windows 8 the typical location is here: C:\Users\%username%\AppData\Local\Microsoft

LAST STEP:  Rename the OUTLOOK folder to OUTLOOK.old

Now restart outlook,  rebuild your profile and send and receive as you normally would without messages being stuck in the Outbox 

Hi JanpaulH

We have the same problem I'm hoping your fix resolves ours also.

Regards

Andrew