email stuck in outbox Outlook 2013

Experts,

We have two users that constantly and inconsistently have emails stuck within their outbox. They only realize it when their client is requesting the emails, when they check the email is in the outbox. The problem has become urgent. I have tried everything from creating new outlook profiles, disabling add ins, virus\malware scans,  updating nic drivers.Opened a case with Microsoft, they ran repairs on exchange, deleted and moved mailbox to different store, enabled logs to catch the issue, nothing has worked so far. Thanks in advance for your assistance
jaya31Asked:
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Will SzymkowskiConnect With a Mentor Senior Solution ArchitectCommented:
*Correction it was my Second Post that i mentioned this.

Will.
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Will SzymkowskiSenior Solution ArchitectCommented:
Is it only specific users? Did you upgrade from an eariler version of Exchange? If you use OWA does it work?

Will.
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jaya31Author Commented:
Hi Will,

Yes it is only happens to specific users 3 total. Yes the issues only started to happen when we upgraded from office 2007 to office 2013. One user specifically told me that she never had an issue in Outlook 2007
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Will SzymkowskiSenior Solution ArchitectCommented:
If this only happens with 3 people can you just do the following...
- export the users entire mailbox (New-MailboxExportRequest and save as a pst)
- Create a new mailbox for this user
- import the pst file from into the new mailbox (NewMailboxImportRequest)

I say this because there are not a lot of users involved and this will save time in the long run.

Also if there users login to another machine does Outlook work properly for them? It may not be the Outlook profile as you have stated that you have already tried re-creating it but maybe the Windows Profile.

Will.
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jaya31Author Commented:
ok,  I will try that. We didn't have the users log on to another machine as the problem is so inconsistent. I will try your method above and see if that works. It must have something to do with the upgrade from office 2007 to 2013.
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Praveen Kumar BonalaProgrammer AnalystCommented:
Hi,
Uncheck the cached exchange mode and see what is happening. I am not sure it will work but just trying in this way....

one more thing open email account settings and go to more settings, select connection tab and uncheck Connect To Microsoft exchange using HTTP.
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jaya31Author Commented:
Hi Praveen,

Both of those options are unchecked. We never used cached mode, all users are online mode. Any more suggestions? Thanks.
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maher khaleefaCommented:
try to send through owa is mail stuck or sent ?
after you upgrade did you check outlook version as minimum supported version for exchange 2013 are the following
The following versions support Exchange 2013
Outlook 2007: 12.0.6665.5000 (SP3 + the November 2012 Public Update or any later PU)
Outlook 2010: 14.0.6126.5000 (SP1 + the November 2012 Public Update or any later PU)
Outlook 2013: 15.0.4420.1017 (RTM or later)
you can find the outlook version by
open outlook->goto file ->help
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jaya31Author Commented:
Hi Maher,

We asked the user to use OWA  and it no issues, but she did not want to use it for more than a day because of functionality. But the problem is so random and inconsistent, that it wont happen for a day or two then it happens, but always to the same three users. Currently running the an updated version of outlook. Very frustrating problem as we cannot find what is causing the issue and Microsoft support could not as well.
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maher khaleefaCommented:
Goto file  account setting  change account
Check if server name is mailbox identity@yourdomain.com or just a name
If identity go to more setting ->connection -> exchange proxy setting
Https:// your fqdn
Check connect using ssl
Check only connect to proxy server write msstd:your mail fqdn name
Proxy authentication basic
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jaya31Author Commented:
Ok, I will try that as well, does this create a more stable connection to exchange?
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maher khaleefaCommented:
The server name must show as hex@domain as new arch of exchange
Previous exchange use basic
Exchange 2013 use ntlm  this sometimes cause problem with send
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jaya31Author Commented:
I checked it and the setting show as servername@domain.com, if so it is suggested to use the secure setting connections
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maher khaleefaCommented:
Great
Then you check account setting
Server name shown as name@domain
Not hex format@domain
This mean cannot find your account path
As connection to mailbox changed from exchange 2010 &2013
Try set thesecurity and test then repair profilw again
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maher khaleefaCommented:
And as work around to map these users  assign your account full control on their mailboxes then open your outlook their accounts will belisted in your outlook and the map will be created
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jaya31Author Commented:
Problem still exists after all the suggestions. Anyone with anymore suggestions.
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jaya31Author Commented:
We recreated the users windows profile. Its been about 2 months with no issues. I think there was something attached to the profile that was affecting it
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jaya31Author Commented:
I've requested that this question be closed as follows:

Accepted answer: 0 points for jaya31's comment #a40765454

for the following reason:

Recreating the profile is the last resort scenario, there may be a more direct answer, but it worked.
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Will SzymkowskiSenior Solution ArchitectCommented:
Based on the comment you accepted as the answer recreated the Windows Profile. I had mentioned doing this in my very first post.

Please accept my answer.
Will Szymkowski2015-01-21 at 14:15:00ID: 40562770

Will.
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jaya31Author Commented:
Hi Will,

Did go through and saw the bullets,  recreating the profile suggestion was at the end and I missed it. I apologize, I will assign these points to you. Thanks.
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jaya31Author Commented:
Recreating the profile solved the issue
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Will SzymkowskiSenior Solution ArchitectCommented:
No worries, things can get over looked. I even had to go back and look cause I thought I had mentioned that but wasn't sure.

Anyways thanks!

Will.
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