Hi everybody,

I am using Outlook 2013 connecting an Exchange 2013 server. After sending a mail, all outgoing mails remain in the outbox. After removing the cache files it works for a while until the problem occurs for the next time (approx. once every two days). 

I already re-installed Windows 8 to test it on a completely clean environment...OWA works fine, the problem only exists with Outlook. 

Additional note: It might be interesting that after sending a mail, the "Send/Receive progress" window states "sending xy@xy.de - complete" but the Mail is still in the outbox and was not delivered to the recipient. Safe mode doesn't work for me. Other users connecting with Outlook 2010 don't have a problem with this exchange server.

Do you have any ideas? If I can provide you with further information, please let me know.

Greets,

Basti

What addins are you using? Antivirus scanners can prevent Outlook from moving messages to the sent folder.

Can any address trigger this behavior or does it happen with certain addresses?

Is this your mailbox or a shared/secondary mailbox?

Thanks for your answer. Here are the requested information:

>What addins are you using?

No 3rd party addins, at the moment "Microsoft Exchange Add-In", "Microsoft VBA for Outlook Addin", "OneNote Notes about Outlook Items" and "Outlook Social Connector 2013" are activated. But the problem also occurs if no addin is active (or even in Safemode).

>Antivirus scanners can prevent Outlook from moving messages to the sent folder.

I will try to deactivate the virus scanner the next time. (Avira is used)

>Can any address trigger this behavior or does it happen with certain addresses?

No, it does happen with any address by random. Once the problem occurs, I can try to send as much mails as I want to any address - nothing leaves the outlook client.

>Is this your mailbox or a shared/secondary mailbox?

It is a user's mailbox, nothing shared.

• Edited by basti01 Friday, May 31, 2013 3:07 PM

Thanks for your answer. Here are the requested information:

>What addins are you using?

No 3rd party addins, at the moment "Microsoft Exchange Add-In", "Microsoft VBA for Outlook Addin", "OneNote Notes about Outlook Items" and "Outlook Social Connector 2013" are activated. But the problem also occurs if no addin is active (or even in Safemode).

>Antivirus scanners can prevent Outlook from moving messages to the sent folder.

I will try to deactivate the virus scanner the next time. (Avira is used)

>Can any address trigger this behavior or does it happen with certain addresses?

No, it does happen with any address by random. Once the problem occurs, I can try to send as much mails as I want to any address - nothing leaves the outlook client.

>Is this your mailbox or a shared/secondary mailbox?

It is a user's mailbox, nothing shared.

• Edited by basti01 Friday, May 31, 2013 3:07 PM

• Safe mode doesn't change anything, problem still exists
• Deactivating virus scanner doesn't change anything, mails still stay in the outbox folder
• If I move a "stucked mail" from the outbox to the draft folder and log-in into OWA, sometimes it is possible to send this (same) mail directly, sometimes it is not and I have to create a new mail and copy the content.

Do you have any further ideas?

This could be caused by a corrupted OST file, so disable Exchange Cached Mode and recreate the OST file.

• Edited by ShEiQh Tuesday, June 18, 2013 10:20 PM

This could be caused by a corrupted OST file, so disable Exchange Cached Mode and recreate the OST file.

• Edited by ShEiQh Tuesday, June 18, 2013 10:20 PM

Thanks for your answer but this is what I already tried. Removing the OST cache file and let outlook download everything again doesn't help here. The problem still shows up after a couple of days...

Perhaps the following link may help...

http://www.slipstick.com/problems/common-problems-that-cause-email-to-stay-in-the-outbox/

Do the messages send if you don't look in the outbox? The onenote addin is one of the addins that causes the most common problem: messages marked as read when you look in the outbox. (iCloud & antivirus will do the same.)

@Sheiqh, thanks for the link but there was nothing new behind it. 

@Diane Poremsky

It doesn't matter which folder is currently shown when the problem occurs. I am working most of the time in the inbox folder and the problem occurred there too.

I now created a completely new user account in the Active Directory and assigned a new mailbox on the Exchange server. Will see if this works after importing the created pst file (which I exported before)...

Sheiqh

Try to fix it, open the ECP and navigate to mail flow -> receive connectors. Double click Client Frontend . Go to the security tab and under permission groups, tick Exchange servers. Click save.

delete the e-mail that was stuck in Outbox, but after restarting Outlook, new e-mails were being sent to internal recipients like they were supposed to.

Hi Basti,

I have exactly the same problem with a client of ours.

Exchange 2013 CU2 with Outlook2013, Exchange on Server 2012, Outlook on Terminal Server 2012.

Every once in a while, sent mails stay in Outbox. The attribute of the mail says "sent" and most of the time the mail is indeed sent correctly but stays in the Outlook outbox nevertheless.

The behaviour seems totally random. No specific mail adresses, nu specific user, no specific times or dates, no attachment size.

Sometimes mails stay stuck for two minutes and then disappear from the outbox, sometimes it takes two hours.

My client and i are getting very frustrated with this as we can never really tell if and when a mail is being correctly sent or not.

i have made all recommended exclusions in Endpoint security to no avail.

We use no Outlook plugins other than the default ones.

I am convinced by now that this is buggy Outlook behaviour.

Regards,

Patrick

Hi Basti

Did anyone ever find a solution to this?  I am having the same issue on my network and have tried all the resolutions mentioned here without any luck. 

Only difference is that i am running Exchange 2010.

thank you

• Edited by JJinZA Thursday, October 24, 2013 9:46 AM

Hi Basti

Did anyone ever find a solution to this?  I am having the same issue on my network and have tried all the resolutions mentioned here without any luck. 

Only difference is that i am running Exchange 2010.

thank you

• Edited by JJinZA Thursday, October 24, 2013 9:46 AM

Not really a solution but more some kind of workaround: I created a completely new user in the Active Directory as well as a new mailbox. Afterwards, I exported the old mailbox to pst and simply imported the file into the new mailbox. Worked fine for me since only a very small number of users were affected.

We have been having the same issue with our outlook exchange running on windows 2008 for weeks now and have tried several fixes suggested but the issue is still ongoing and losing us business..... Is there a solution from Microsoft or it is a bug?

Hi Patrick Have you found a solution or received one from MS that works? We are having similar issues and the frustrating thing is it's not consistent re time of day or user.... Many thanks for any help, Johnjbrussell

Please right click on outlook icon in the system tray while holding the ctrl key and select connection status. Review the results let us know if you see any errors. Test email Autoconfiguration and Review the results.

I doubt your problem is described here, but I am curios to see what happens with your user's connection status in outlook when messages get stuck?

https://support2.microsoft.com/kb/2663435?wa=wsignin1.0

• Edited by net_tech Saturday, October 04, 2014 2:41 AM

Please right click on outlook icon in the system tray while holding the ctrl key and select connection status. Review the results let us know if you see any errors. Test email Autoconfiguration and Review the results.

I doubt your problem is described here, but I am curios to see what happens with your user's connection status in outlook when messages get stuck?

https://support2.microsoft.com/kb/2663435?wa=wsignin1.0

• Edited by net_tech Saturday, October 04, 2014 2:41 AM

How many of these users also have Icloud installed?

We are having much the same issue with one user.  She has Icloud so that she can synch her mail with her outlook system, her phone and her Ipad.

We found that if she forwards the mail it will often get sent, but the original mail remains stuck in the outbox.

We also found that removing Icloud eliminates the issue, but that is not a good solution due to the iphone and the ipad in the loop.

Was hoping someone had found a solution to this aggravating issue.

We have another user that is using Outlook and Icloud with no issues.

One other variable that may be an issue is a program called CompanionLink that the user was using when she had an android phone.  We have removed CompanionLink and reinstalled Icloud, but nothing seems to help the situation.

Does anyone know how to manually remove all traces of Icloud so we can try to move forward from there without doing a complete wipe on her system?

I had the same issue with an Outlook 2013 client in Online Mode. All outgoing mails were stuck in Outbox folder.
The issue occured because it seems that Outlook, also with cache Mode disable, needs a Cache File (OST) for the primary account.

To resolve my issue, i temporarily enabled the cache mode and started outlook for about 5 seconds until it created a small .OST File. Then I disabled the cache mode. After that sending out mails works without any problems.

Regards
Simon

• Proposed as answer by Simon Tauber 22 hours 43 minutes ago