Inability to "Send-As" for users of Exchange 2007

by on Feb.01, 2009, under Windows Info

We’ve recently run into a situation that we realized is no longer possible when running Exchange Server 2007 on Windows Server 2008.

You cannot choose an alternate email address from which to “Send-As”, because the Exchange server will resolve your user object against the Active Directory, and replace whatever alternate address you’ve chosen with your user object’s default email address, as listed in the Active Directory.

Here’s the scenario-
Fabrimak is a company with many divisions. All of these divisions function as individual companies, and as such, have their own corporate identities, domain names, URLs, etc. However, due to the current trend of downsizing and leaner operational costs, they share a core Active Directory domain namespace, running Windows Small Business Server 2008 Premium Edition.

I know this is starting to sound like a test question for an MCSE exam, but bear with me.

The domain names in use currently are as follows:
Fabrimak.local (internal domain)
Tailswimtoys.com (default Internet domain in Exchange)
Consoto.com
Northbound.us

So, when users of Fabrimak’s internal network open up Outlook 2007, and create a new outgoing email, manually select to show the “From:” field, and choose to use their ‘user@consoto.com’ address, the mail recipient sees that the email came from ‘user@tailswimtoys.com’. This is because the outgoing email address used is decided when Outlook resolves the user account used to log into Exchange against the Active Directory, returning whatever address is listed as the user’s default. (Usually managed in the Exchange Console with the Recipient Update Policy.)

Even if you choose to show the “From:” field, and select an alternate (albeit valid) email address, the Exchange server will change the outgoing address used to your user account’s default outgoing email address.

Apparently, this ability to “Send-As” was purposefully removed by Microsoft, during the codebase rewrite of Exchange server.

However, (with the help of some friends from Redmond) there is a workaround. Allowing this “Send-As” behavior *is* possible. The workaround entails the use of Mail-Enabled Distribution Groups, and the removal of the Recipient Update Policy from the user account.

Details coming in my next post.

:,

4 Comments for this entry

  • Rick

    Brian,

    Like many, I was disappointed to find this bizarre change.

    I use Distribution Groups to determine which alias the original message was sent to, for “incoming” mail.

    While my account has “Send As” permissions for the alias address, however, the reply address is changed from the “alias” address to my primary Exchange address…as you describe.

    Just curious about any workarounds you might recommend, and glad you made this post…I thought I was losing my marbles with this change!

    Thanks in advance,

    Rick

  • brian

    Hi Rick,

    Welcome! Yes, read on… The post after this one details the workaround. Basically, you need to remove the Recipient Update Policy from your user account *and* from the Mail-Enabled Distribution Group. Then, when composing a new email, select the distribution group you created for the alternate address for your “From:” address.

    Lemme know if you get it working, or if you need help.

    Brian

  • Kevin

    Brian,

    Is there any post that is explaining this “send-as” problem.
    I mean that will explain me how to fix this.

    Kevin


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