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Email stuck in outbox when sent to address outside of Exchange domain while using roaming profile on 2008 Terminal Server.

Posted on 2013-01-25
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Last Modified: 2013-03-09
I have four users out of about 130 with the following problem.  When they send an email to someone outside of our Exchange 2010 domain, the message gets stuck in outbox.  This happens when they are using Outlook 2007 on 2008 R2 RDS, roaming profile, and redirected services.  OWA works fine. Using a standard workstation works fine with same roaming profile and redirected folders.  Safe mode works for two of the users.  Also works if a user does a right-click to send a file as an attachment instead of opening new message and adding file.  Deleting roaming profile works for a short time.  One user has rare occurrence when email get sent correctly.  All users have same configuration.  

Any ideas?
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Question by:joseph6478
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by:Coralon
ID: 38823245
It sounds like they are getting multiple outlook profiles created.  I have run into this before, and the profiles simply refuse to send out email.  The solution was to delete all of the profiles, and recreate a new one.  If that fixes it, then your next step is to determine where the multiple profiles are coming from.

Coralon
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by:Manpreet SIngh Khatra
ID: 38823988
Could be a corrupt machine profile causing the issue if all others with the same configuration are working fine

- Rancy
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by:Brian B
ID: 38827353
Sounds like a profile issue to me as well, but that's been covered. Also if you are using caching, find the OST associated with that user and delete it.
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joseph6478 earned 0 total points
ID: 38890809
I ended up contacting MS about this.  It appears they found something in logs that they have created a hotfix for that will be released in next few weeks.  So I will wait until then to see if the fix works.

Thanks for input.
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by:Manpreet SIngh Khatra
ID: 38891931
So you made MS create a Hot-fix :) 'jokin'

- Rancy
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by:Brian B
ID: 38954620
Glad you found a fix. Thanks for posting the solution.
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Author Closing Comment

by:joseph6478
ID: 38968941
I used the following MS Hotfix to solve the problem.

http://support.microsoft.com/kb/2760822
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