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E-mail showing Exchange address instead of SMTP address intermittently

Posted on 2012-09-12
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Last Modified: 2013-03-13
I have a user that occasionally has her Exchange address show up in e-mails rather than her SMTP address. Mail delivery is working fine and it's not effecting Outlook in any way. I've tried to figure out what may be causing this to happen but have not had any luck. The user is Office 365 and Outlook 2010 in cached Exchange mode. An example of what she is seeing is below:

From: /O=EXCHANGELABS/OU=EXCHANGE ADMINISTRATIVE GROUP (FYDIBOHF23SPDLT)/CN=RECIPIENTS/CN=B7383C98665140A59F783DDB557E5E79-SOMEONE@MYORGANIZATION.ORG On Behalf Of Someone Important
Sent: Wednesday, July 18, 2012 8:29 PM
To: 'outside1@outsideorganization.org'
Cc: outside2@outsideorganization.com
Subject: Second round of stuff

Does anyone have a suggestion as to the cause or a way to prevent this from happening. Internal user's will also see this from time to time but it is not consistent.
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Question by:MarkInAusTX
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LVL 52

Expert Comment

by:Manpreet SIngh Khatra
ID: 38391170
Is the user also sending on behalf of some other account with the Outlook ... if so maybe its trying to send with the other account if she is replying to messages ?

- Rancy
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Author Comment

by:MarkInAusTX
ID: 38391219
Rancy:

I don't believe the user is sending on behalf of anyone else but that is a good suggestion. I will check to see if that is a possibility.
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LVL 52

Expert Comment

by:Manpreet SIngh Khatra
ID: 38391296
From: /O=EXCHANGELABS/OU=EXCHANGE ADMINISTRATIVE GROUP (FYDIBOHF23SPDLT)/CN=RECIPIENTS/CN=B7383C98665140A59F783DDB557E5E79-SOMEONE@MYORGANIZATION.ORG On Behalf Of Someone Important

I asked that because of the Bold details you can see above :)
Does the user uses any Handheld ?
Does she works with VPN or Internal ?
Did you check with Upgrades to her outlook ?
What is her OST or PST's any she uses ?

- Rancy
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Author Comment

by:MarkInAusTX
ID: 38391329
I see what you mean. That's the interesting thing - she is sending as herself. To make it clearer, he is what it looks like:
From: /O=EXCHANGELABS/OU=EXCHANGE ADMINISTRATIVE GROUP (FYDIBOHF23SPDLT)/CN=RECIPIENTS/CN=B7383C98665140A59F783DDB557E5E79-ALEX@ABC.ORG On Behalf Of Alex Smith

The user has an iPhone with an ActiveSync connection to the mailbox.
It is an Office 365 account, no VPN and it's the same when she works from the office.
All the latest updates to Outlook have been applied, including those Office 365 installs during account setup.
She has an OST file and no PST files. All her data fits into the Office 365 mailbox at this time.
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Expert Comment

by:Manpreet SIngh Khatra
ID: 38391496
Does the user has "Send-on-behalf" rights to "Alex Smith" ??

- Rancy
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Author Comment

by:MarkInAusTX
ID: 38404128
Rancy,

I guess the answer is yes. Alex Smith can send as Alex Smith. The user is sending messages from her own mailbox.
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LVL 52

Expert Comment

by:Manpreet SIngh Khatra
ID: 38970564
Is the issue fixed or what happened

- Rancy
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Author Comment

by:MarkInAusTX
ID: 38982679
Rancy:

Sorry for not following up. The issue was never fixed. A little over two months ago, the user's laptop was damaged and had to be replaced. Since replacing the laptop, the issue has not occurred. I can only assume it was something hokey with the Outlook profile and now that the user has a fresh Outlook profile, the problem is gone.

I wish I knew what it was. This user's account was migrated from an on-premise Exchange 2007 to Microsoft BPOS and then to Office 365. All I can think of is that through the three migrations, something affected the profile.
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Accepted Solution

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Manpreet SIngh Khatra earned 800 total points
ID: 38982808
I can assume few things

- Outlook profile or installer issue
- Machine profile issue or OS issue

Also as its done you should close the post :)

- Rancy
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Author Closing Comment

by:MarkInAusTX
ID: 38983015
Rancy was helpful during troubleshooting. Thank you for the help.
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