Mail Merge - Sent but still in Outbox

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First of all thanks for taking the time to read this thread.

I have a user that's doing a mail merge and the email was sent (from an Exchange server to a yahoo address) however the email remains in the Outbox. Why would a sent mail merge continue to show in the Outbox after successfully being sent?

The user and I both expect this message to show in the Sent Items folder after being sent. Is there a setting that can correct this or a reason for this? I would hate to ask the user to manually move the messages to the Sent Items folder.

Mucho mahalos in advance for your time and reply!

On a side note, I did do a search before posting and noticed a thread titled "Sent emails remain in Outbox" in which Diane replied about a possible KB article but nothing has been posted since 2009.
There is no setting and the usual cause is poor network connection to the Exchange mailbox or issues with an antivirus scanner scanning messages you send. If you log in to OWA, is the message in the Sent folder? If so, you can delete it from the outbox.

I'm assuming the problem is not limited just to messages being sent to yahoo addresses, but for any mail merge?

Way to think outside of the box as I would've never thought to check the OWA Sent Items folder!

You're correct and it does show in the Sent Items in OWA so this would indicate something on the machine possibly

(anti-virus as you mentioned). I would like to think the connection to the server is solid as she's running at gigabit speeds and the server is not 20 feet from her but I'll explore that as well. Ping times are not fluctuating at all.

I'm not certain this is only a problem with Yahoo as its the only 3rd party account I've tried. I just wanted to be sure I posted enough info for you to make an educated guess.

I will open a case with McAfee and let them chew on this as they have a plug-in that does scan our messages.

Thank you, thank you, thank you! :)
I'm sure it can be a problem with any domain, not just yahoo.

If you use client side virus scanner on outgoig email, its probably that. Choices are disable email scanning (recommended) or delete the items in the outbox every now and again... You can do a test by opening Outlook in Safe mode and see if it happens. (Close Outlook. Hold Ctrl as you click on the Outlook icon to start in Safe mode.)

It could also be a corrupt cache. You could delete the ost and let outlook rebuild it, or, if the ost is large, do nothing and clean the outbox out every now and again.

This doesn't only happen with Yahoo, as suspected.

Starting Outlook in Safe Mode allows the mail merge to be successfully sent and then show in the Sent Items folder; it does not get stuck in the Outbox.

I will follow up with our email scanning provider.

Many, many thanks to Larry and Diane for their help and I hope someone will find this thread helpful in the future!
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
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