For this particular exercise, let’s pretend that you are, once again, named Bob. You work for TailswimToys.com, and they use a Microsoft Windows Small Business Server 2008, running Exchange 2007 for email and collaboration services. You use Outlook 2007, and are very happy with it overall.

All of your customers know you as bob@tailswimtoys.com [eat that, spammers… ;) ]

Recently, TailSwimToys experienced a huge economic windfall, and acquired Fabrimak.com, whose main business model is appearing in test questions, under an altered name.

Anyway, bob@fabrimak.com needs the ability to communicate with Fabrimak’s customer base without letting them know that he is *also* bob@tailswimtoys.com, which they would view as silly, thus undermining their confidence in Bob. (And Bob’s company)

In order for Bob to send an email from an address other than his default email address, you need to do the following:

Note: You may want to stop all inbound email services while you do this. This way, anyone sending email to an address that you’re moving to a distribution group will not bounce, but will sit on their mail server in the retry queue, and will be delivered after you’ve created the group, and re-started the inbound mail services. (typically, you’ve got 12 hours before an email will expire from the queue and cause a NDR.)

This assumes that you’ve already configured your Exchange server to accept email for the Fabrimak.com domain, and all necessary DNS records have been created, as these are beyond the scope of this post.

First, open the Exchange Management Console, and delete all but the default email address from the user’s mailbox. (leave bob@tailswimtoys.com in there, this will be the email address used when Bob doesn’t specify an outbound address.)

Next, remove the Recipient Update Policy setting from the user’s mailbox in the Exchange Management Console. This is necessary so that the alternate addresses aren’t re-applied to the mailbox on the next run of the Recipient Update Service.

Then, create a Mail-Enabled Distribution Group named bob@fabrimak.com, and apply the secondary email address to it. (in this case, bob@fabrimak.com) Make the user Bob a member of this group. Also, you’ll need to grant Bob “Send-As” permissions to the Mail-Enabled Distribution Group, so he can “Send-As” from the Group. Another thing you’ll need to do is remove the Recipient Update Policy setting from the Mail-Enabled Distribution Group, as it’s enabled by default.

After these configuration changes, Bob will be able to compose a new email, select to show the “From:” field in Outlook, click “From:”, and select the Mail-Enabled Distribution Group named “bob@fabrimak.com”, and that is the only address for Bob that the receiving party will see.