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Why send from different email address doesn't work?

Posted on 2016-10-31
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Last Modified: 2016-11-11
This is using MS Exchange 2010 server. This Exch server is hosing few public email domains, for example, @abc.com, @def.com, etc. @abc.com used to be the primary email domain. Recently, we purchased and successfully registered for a new public email domain, called ghi.com. This new email domain also successfully configured in exch as accepted domain, plus some other mx settings in NS server. We verify that mails sending/receving from this new @ghi.com is working fine.

However, if we added this @ghi.com as the secondary smtp email address besides existing @abc.com, then mails failed to send out. For example, userA already got userA@abc.com configured in his mailbox. Now, we added userA@ghi.com as the secondary email address in userA mailbox property.

Then on UserA MS Outlook, we create additional From email address, called userA@ghi.com. Now, when replying email, userA can choose between send as userA@abc.com or userA@ghi.com. Mails sending as userA@abc.com works perfectly. However, attempt to send as userA@ghi.com, failed with following error:

You can't send a message on behalf of this user unless you have permission to do so. Please make sure you're sending on behalf of the correct sender, or request the necessary permission. If the problem continues, please contact your helpdesk.

Any configuration step i missed out? Any help is appreciated.
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Question by:MichaelBalack
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Expert Comment

by:Niten Kumar
ID: 41867885
Go to EMC and search the mailbox userA@ghi.com, right-click on it and go to Properties.  Select Mail Flow Settings tab and click on Delivery Options and then properties. Add the userA@abc.com account here and apply OK.  Hopefully you have assigned Manage Full Access Permission the userA@ghi.com mailbox.
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by:mbkitmgr
ID: 41867967
From memory Send As only looks at the Primary Email address of the mailbox.  For example if your primary is fred@contoso.com and you have a secondary email address of fred@companyb.com, OLK and Exchange only evaluate the primary -  int his case the contoso email
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by:Simon Butler (Sembee)
ID: 41868736
Exchange doesn't work like that.
As far as Exchange is concerned, all mailboxes only have one email address - the default. You cannot pick and choose from different ones. Any other email addresses are aliases for INBOUND email only.

If you have multiple domains then you have a number of options to be able to use different addresses for outbound email...

1. Additional account. Create a new mailbox in Exchange, with the required email address. Give the primary user full mailbox and send as permissions. Add to Outlook 2010 or higher as an additional ACCOUNT, which gives you signatures, rules etc.

2. Dummy account method. I don't like that route, but some do - this is where you add additional POP3 accounts to Outlook.

3. Third party tool choosefrom by ivasoft.biz - which allows you to pick and choose the email address that you want.
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Author Comment

by:MichaelBalack
ID: 41871445
Hi Niten,

Besides Full Access, I granted UserA@abc.com with "Send As" permissions. However, UserA still can't send mail as usera@ghi.com, although others work perfectly.
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Author Comment

by:MichaelBalack
ID: 41871447
Hi mbkitmgr,

Precisely, added userA@ghi.com as secondary email address only enable the inbound mails work. However, mails sent out still presented as usera@abc.com.
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Accepted Solution

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MichaelBalack earned 0 total points
ID: 41871457
Hi Simon,

I agreed with you for number 1. The concept should goes this way. Think nothing else we should set on the Exchange Server EMC side.

Now, when I tried to sent as userA@ghi.com, the mail sent out successfully. Think this has to be done with the OAB (delete it and get the latest ones), and maybe also the autocomplete.

The 3rd one being this new email address only appear in GAL few days after creation. Now, I can see that userA@ghi.com shown in the GAL, while it didn't few day ago.
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Expert Comment

by:Simon Butler (Sembee)
ID: 41871754
The OAB is only updated once a day by default.
The Outlook client will only download the OAB once a day or when the client is restarted. Therefore it can take a day or more for changes to the OAB to be seen.
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Expert Comment

by:Simon Butler (Sembee)
ID: 41873689
I am objecting to the question being closed in the way requested.
The original question was about using a different email address on the same account, which I pointed out wasn't possible. It had nothing to do with the OAB.
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Author Comment

by:MichaelBalack
ID: 41881812
Hi Simon,

The problem wasn't on Exchange Server setting for the new email address. it was on the client outlook side. I can think of these few things that led to the failure:

First, new email address does not appear on the GAL immediately. I think there is a EMS powershell  cmdlet for it to update manually.
Second, OAB has to be removed, and select to download a whole piece, otherwise, it won't work
Third, some said (forums) removes the existing autocomplete

This was what I experienced and did to make it works. I appreciate the suggestion you made on the Exchange server side, but this alone, doesn't going to work as the main part is still the client outlook side for the above 3 considerations.
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