Emails stuck in Outlook outbox

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Outlook version
Outlook 2010 32 bit
Email Account
Exchange Server
Hello All - This is my first post.

The problem I have appears to be well known but even after spending several evenings trawling the net I cannot find a solution.

Sometimes when, say creating a new email and pressing send, it arrives in the out box with the "Sending Message Icon." In this case it will go off OK when pressing send and receive.

However, sometimes it arrives in the out box with the "Draft Icon" in which case it will never go out.

If I open the email and copy every part of it into a new email form it will then arrive at the out box with the "Sending Message Icon" and everything works OK. - But the original with the "Draft Icon" is still stuck in the out box.

I can't find a way to change the "Draft Icon" to a "Sending Message Icon" in the out box and I cant find out why Outlook sometimes saves the email to the out box with a "Draft Icon."

One other point, An email in the out box with a "Sending Message Icon" if highlighted by clicking it will immediately change to "Draft Icon" and then will not be sent.

Outlook icons can be seen here:

This problem does not occur when running Outlook in SAFE mode.

Furthermore, any emails that are stuck when running normally can be opened in safe mode and then "sent" They go out without a problem. I can't do that in normal mode.

Presently about 75% of my emails have to be opened from the out box and copied in order to send them.

I need to corect this problem but if all else fails, as this is very frustrating and time wasting is there any way to repair or reinstall Outlook. I have run the repair function from the original Office 2010 installation disk but that did not solve the problem.

I am running Outlook 2010 (part of the Office 2010 suite of programs) under Windows 7 Ultimate and Exchange SBS 2003 on the server. This did not happen when I ran Outlook 2003 that came with SBS 2003. No one else in our office has the problem - but none are running Outlook 2010.
Thanks for that Diane,

There's a lot of information to take note of, but for now I can say that in a short test new emails do appear to go out OK if I don't look in the out box. But this problem first came to light a few weeks back when I saw that replies to received emails were still in the out box after several days - I was not then in the habit of looking in the out box, I noticed that in the folder list, Out Box had a number against it which should not have been there as I do an automatic send every 5 minutes. So I am not sure yet if looking in the out box is the cause - I think it sometimes happens anyway. I have been on holiday today so I have not used Outlook until I came home this evening. It will get a more thorough testing at work tomorrow.

I have however run MFCMAPI and can confirm that there was nothing in the root Store.

I will respond as I progress.
What addins do you have installed? If it is the 'looking in the outbox' problem, it's caused by an addin.
I have had numerous issues with Outlook 2007 including emails being stuck in the outbox and difficulty opening the program.

I'm considering upgrading to the 2013 version - do you think that I will have less trouble with the new version?
Generally speaking, upgrading will not fix problems. Problems will often go away, but that is because of the new install or new profile, not the upgrade.

Check these two articles, then try repairing the installation.

Stuck mail is often due to an addin. Common causes of stuck mail

Outlook is slow

if you are looking for an excuse to upgrade, then go ahead... there is a good chance your problems will go away. :0
I found a solution to this same problem. The problem started shortly I upgraded from Outlook 2003 to 2010. The solution I found for Outlook 2010 after many trial and error is this:

1 Before you click the SEND box in the new email to send out, make sure the Outlook program running in another window is set to the OUTBOX. This is the key for this to work.
2 Then click the SEND box in the email you created.
3. I then go to the OUTBOX and click SEND/ RECEIVE and it now sends it out each and every time.

If I forget to make sure that Outlook is open to the Outbox, then what I created won't send out, and I have to recreate the email over and do it right.

The permanent solution "might" be to reinstall Outlook 2010, but thats a pain and who knows what other problems may come from that. Hope this helps.
There is something wrong if mail only sends if the outbox is open - it's not unusual for it not to send if the outbox is open (messages get marked as read if the outbox is open).
I have read your reply and have tried going to my Outlook 2010 to check that it is open. Unfortunately the ten emails are still hung up in the Outbox. Any other suggestions to clear them?

Larry Mosher
League City, TX
do they send if you use safe mode?
Are they bold and italic (so ready to send)?

To open Outlook in Safe mode: Close Outlook then hold Ctrl as you click on the Outlook icon. You'll get a message asking if you want to start in Safe mode. Click Ok.
i have the same problem. its a joke. im starting to hate microsoft. GMAIL all the way!!!
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