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User is unable to send emails on behalf its manager. issue happens randomly

Hello MS team,

I need from your expertise to resolve an issue that happens randomly to one of our executive admins.

The problem she is facing is that she is unable to send email on behalf her Manager, the email is sent but the message is delivered with her name instead of her manager. We fixed the issue last week, by removing/re-applying permissions, delegates, and so on, but today she experienced
same issue. Whenever she tries to send an email on behalf her manager, the email is sent but with her name. Please see troubleshooting steps below followed at server level and from client level.

Just to clarify this only happens to her, there are other delegates under Manager's mailbox with same level or permissions and they are OK. Like a said, this is a ramdom issue, something works
and sometime isssue reocurrs


Troubleshooting followed so far:

At client level:

With Outlook and Lync clients closed, go to windows explorer, C:\Users\xxxx\AppData\Local\Microsoft\Outlook, then delete all OST files under each outlook folder, and delete Offline Address book.

From control panel, mail32 bits, delete all outlook profiles.

Reboot laptop.

From Manager's laptop, open outlook, click on File, account settings, delegate access, and remove ExecutiveAssistant's account.

Allow up to 30 minutes to replicate all changes in Exchange.

Log into  domain.

Open Outlook, and setup a new outlook profile.

Click on send/receive tab from outlook menu,  send and receive group, and click download address book. Allow up to 10 minutes to replicate changes

Verify executive's account user is unable to see Manager's mailbox, then  to re-add right permissions [Full Access, Send of behalf].

From Manager’s computer, open outlook, click File, account settings, delegate, verify executive assistant is under delegates, and make sure she has editor permissions.


At server level:

From Exchange management console, expand recipient configuration, click Mailbox, and find Manager's mailbox.

Right-click Manager's mailbox, click Full access permission, and remove Exec's Account.

Right-click Manager's mailbox, click mail flow settings, delivery options, then properties. Remove Exec's Account from send on behalf options, click Apply, OK.

Right-click Manager's mailbox, click Manage send as permissions, remove Exec's Account, click Apply, OK.



Our environment as per below:

2 Exchange 2010 SP3 CAS servers, one for each location. All of them are VMs, and run Windows 2008 R2

2 Exchange 2010 SP3 MBX/UM servers, one for each location, and both are VMs. Windows 2008 R2 is the OS with latest updates as per above

Our domain and forest level is WIndows 2008 R2

Outlook clients is mixed Office 2010 latest SP and Office 2013


Reference:

How to send an email on behalf another user in Exchange 2010
http://www.inf.aber.ac.uk/advisory/faq/578/

Send on behalf
http://social.technet.microsoft.com/Forums/office/en-US/c4feb86b-76f2-43a7-8b40-68d05f38816b/outlook-2010-question-send-on-behalf-or-send-as?forum=outlook

Send on behalf
http://social.technet.microsoft.com/Forums/office/en-US/6fe8327f-4f11-4f3a-8d0b-0889a67cb230/exchange-2010-error-for-send-on-behalf-with-linked-mailboxes?forum=exchangesvradminlegacy
0
Jerry Seinfield
Asked:
Jerry Seinfield
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1 Solution
 
Simon Butler (Sembee)ConsultantCommented:
Important point missed - is this to internal or external recipients?

Simon
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Jerry SeinfieldAuthor Commented:
internal recipients, one internal user is unable to send on behalf from another internal user
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Simon Butler (Sembee)ConsultantCommented:
Going back through the question, I see this:

"Right-click Manager's mailbox, click Manage send as permissions, remove Exec's Account, click Apply, OK."

You should set EITHER Send As or Send on Behalf of. Not both.
Therefore if the assistant has Send As permissions, remove that.

Simon.
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