?
Solved

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

Posted on 2014-04-25
7
Medium Priority
?
3,210 Views
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.
0
Comment
Question by:jtgerdes
[X]
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
7 Comments
 
LVL 4

Expert Comment

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
0
 
LVL 42

Expert Comment

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.
0
 
LVL 74

Expert Comment

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.
0
What does it mean to be "Always On"?

Is your cloud always on? With an Always On cloud you won't have to worry about downtime for maintenance or software application code updates, ensuring that your bottom line isn't affected.

 

Accepted Solution

by:
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.
0
 
LVL 74

Expert Comment

by:Jeffrey Kane - TechSoEasy
ID: 40054972
FYI, Moderators don't close questions, you do.  Just accept your last comment as the solution.
0
 

Author Closing Comment

by:jtgerdes
ID: 40071920
Did not find solution from other experts' responses.
0

Featured Post

Office 365 Training for IT Pros

Learn how to provision tenants, synchronize on-premise Active Directory, implement Single Sign-On, customize Office deployment, and protect your organization with eDiscovery and DLP policies.  Only from Platform Scholar.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

This article will help to fix the below error for MS Exchange server 2010 I. Out Of office not working II. Certificate error "name on the security certificate is invalid or does not match the name of the site" III. Make Internal URLs and External…
A couple of months ago we ran into an issue that necessitated re-creating our Edge Subscriptions. However, when we attempted to execute the command: New-EdgeSubscription -filename C:\NewEdgeSub_01.xml we received an error indicating that the LDAP se…
This video shows how to quickly and easily add an email signature for all users on Exchange 2016. The resulting signature is applied on a server level by Exchange Online. The email signature template has been downloaded from: www.mail-signatures…
A short tutorial showing how to set up an email signature in Outlook on the Web (previously known as OWA). For free email signatures designs, visit https://www.mail-signatures.com/articles/signature-templates/?sts=6651 If you want to manage em…
Suggested Courses
Course of the Month7 days, 19 hours left to enroll

765 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question