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Outlook 2013 won't send messages until closed/reopened. (With Office365)

Posted on 2014-04-25
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Last Modified: 2014-05-17
We have a client who is using Office365 for email and this particular user has a new Windows 7 laptop and Office 2013 (the license included with Office 365.)  All Windows and Office products are up-to-date.

The issue is that when she opens Outlook and works, it seems to lose connectivity to Office 365 after 10-15 minutes.  Sometimes it says "Synchronizing folder" in the status bar, sometimes it says "Trying to connect to Exchange."  Either way, emails she tries to send queue in her outbox until she closes Outlook and reopens it and it reconnects to the server and sends the messages.

I've been on the phone for hours with Office 365 support and have run all the Exchange/Office365 connectivity tests, created new Outlook profiles, and tried using another network and hotspot to eliminate any network issues.  The user does use the SonicWALL Global VPN Client occasionally, but the issue occurs regardless of whether the VPN connection is connected or not.

Has anyone had any similar experiences?  Can anyone think of further troubleshooting steps?  Microsoft support just wants me to create a new Windows user profile.

Thanks.
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Question by:jtgerdes
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by:wsawalhi
ID: 40023192
Hi jtgerdes,

Have you run the Sign-In Assistant installation from the portal on your machine? Often times connectivity issues occur because the sign-in assistant either hasn't run or hasn't run properly because of a missing pre-requisite. I would recommend re-running the sign-in assistant to see if you can run through the installation without error. Give that a shot and let me know what happens.

You can download it when you sign in to Office365.

Thank you,
Sam
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by:Vasil Michev (MVP)
ID: 40024203
Have you tried Outlook in safe mode? In most of the cases it's usually some 3rd party addon that is causing problems. Do the messages send OK via the OWA? Have you tried it on another machie?

Here is one very detailed article which explains how messages are actually sent and what can cause them to be stuck in Outbox:

http://blogs.technet.com/b/office_resource_kit/archive/2013/08/15/the-mysterious-outlook-outbox.aspx

Normally, none of these will apply, but if you have ruled out network/machine/addons, you can check it. The PDF on the bottom has even more info if you are interested.
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by:Jeffrey Kane - TechSoEasy
ID: 40027817
I doubt that Microsoft Support wants you to create a new WINDOWS profile.  They most likely suggested that you create a new OUTLOOK profile -- because its quite possible that the offline cache (.ost file) is corrupt.

Creating a new Outlook profile will usually fix issues such as you describe.

The Sign-in assistant is not necessary with Windows 7, so don't worry about that.

I would first ask, though... how large is the user's mailbox and has it had a chance to fully sync to the laptop?  (Or at least as much as will sync with the new 12-month threshold Outlook 2013 uses).  

If the laptop has never been connected to a wired Ethernet network connection, then it's quite possible that the mailbox has never fully synced -- because it is tough to get that done over the air on a 10GB+ mailbox.   It can take upwards of 4 or 5 hours on a wired connection.

So if you do recreate the Outlook Profile -- be sure that the laptop is connected via Ethernet for as long as it takes to fully sync.
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jtgerdes earned 0 total points
ID: 40053696
Hi everybody,

Just to finish out the question, we do have the Office 365 Sign-in Assistant installed.  It hasn't not seemed to alleviate the issue.

We have tried Outlook in safe mode and we've disabled the anti-virus plugin as well.  No change in behavior.

For clarification, we have created several new Outlook profiles, so yes, Microsoft was wanting us to wipe out and re-setup the Windows user profile.  (Nevermind that this is a new user, new laptop, and new profile to begin with.)  :)  Thus, the user's mailbox is 32MB and is fully synced.

The issue occurs over wifi and ethernet at this user's primary location.  Further network/location testing has revealed that it works just fine at other locations with other Internet providers.  We conclude that the issue lies with the user's home internet connection and there's little we can do about the issue for now.

Thanks for all your input.  Moderators, please lock or close this question.
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by:Jeffrey Kane - TechSoEasy
ID: 40054972
FYI, Moderators don't close questions, you do.  Just accept your last comment as the solution.
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by:jtgerdes
ID: 40071920
Did not find solution from other experts' responses.
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