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Exchange 2010 multi tenant multiple email "From" addresses not working


We have an exchange 2010 multi tenant server up and running for quite some time. Everything is working well with one exception. We have several hosted domains where users have more than 1 email address. We can add additional accepted domains and associated email addresses to each user account without issue. The user receives emails from all addresses with no problems as well. However in outlook, after adding both addresses as accounts, we will have an option to change the "from" address to one of the additional email addresses when sending mail. The email is sent and received at the destination, but still with the default "from" address. Changing the from address to any other address listed has no effect. I am at a loss as everything else seems to work perfectly. Any suggestions?

Thank you
2 Solutions
Alan HardistyCo-OwnerCommented:
When you added 'both' accounts to Outlook, how did you configure the accounts?

SMTP/POP3 or Exchange (I need to know for both accounts)?

You can't have two Exchange accounts access the same account with the hope to send out as different email addresses.

You can have one Exchange account and one SMTP/POP3 account, but you will need to disable the Receive part of the account otherwise your mail will end up in an infinite loop.

When you configure an exchange account in outlook, email will always be sent out from the default email address that is set in exchange for that account. Adding the same account in again using a different email address will not work because exchange will just ignore this and send the email out through the default address.
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AdventechAuthor Commented:
Both were configured as RPC over HTTP accounts. I believe the first two responses are essentially on the mark. Its just not possible as we had intended it to be but just to clarify:

Multi-Tenant Exchange 2010

Organization Example

Organization name - Company
Domain - company.com
Accepted domain 1 - sports.org
Accepted domain 1 - airplane.net

User Example

User name - Joe Schmo
Primary email address - jschmo@company.com
Additional address 1 - jschmo@sports.org
Additional address 3 - jschmo@airplane.net

- Outlook is configured with 3 exchange over http accounts.
- All accounts receive mail appropriately
- In Outlook when creating a new email you can activate a drop down in the top left corner that allows you to select a "From" address.
- All choices send with jschmo@company.com as the smtp address regardless of selection.
Alan HardistyCo-OwnerCommented:
It can be done if you follow the guide here:


Make sure you disable the Receive part for the 2nd account.
Alan HardistyCo-OwnerCommented:
Can you please advise what further information we could have given you to warrant an A grade?



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