Selectable Outgoing Email Addresses under Outlook with Exchange

Exchange Server offers great support to receive email addressed to multiple domains, but does not allow users to choose which address they would like to use when sending outgoing messages.

Let’s say John Doe at Company abc.com runs Small Business Server 2003 and has a side business with the domain name xyz.com. John can easily receive email to jdoe@abc.com and jdoe@xyz.com. But when Joe sends an email, the recipient will see it comes from jdoe@abc.com. Joe has no option to send the email so it appears to come from jdoe@xyz.com.

This can be resolved by adding an SMTP account to the Outlook profile on the workstation. While not a perfect solution, it does allow users to select which email address they would like recipients to see. This solution is recommended for small sites where the administrative overhead is low and where only a few outgoing domains need to be selectable.

This solution has the following strengths:

  1. Little or no modification needs to be made to Exchange.
  2. It works great on single Exchange servers and SBS servers.
  3. Email to all domains is still delivered immediately to the user’s Exchange mailbox. There is no need to have separate Personal Folder stores or profiles that users will forget to check and backup.

This solution has the following weaknesses:

  1. The Outlook client will need an account added to the profile of each user that needs to have multiple outgoing addresses. An account will need to be added for each outgoing address (other than the primary). Multiple Outlook profiles on one computer or users that use Outlook on multiple computers will increase the administration burden.
  2. While the alternate email address will show on the recipient’s copy, the email headers will still show the Exchange server’s primary domain. Most recipients won’t even know how to check email headers, but this solution is not appropriate when the appearance of complete separation of the domains needs to be achieved.
  3. Outgoing addresses are not selectable under Outlook Web Access.
  4. Outgoing email will always show the user’s primary address unless an alternate is selected. The user must select the alternate SMTP account even when replying to an email sent to the alternate email address. For example, John receives an email sent to jdoe@xyz.com (his primary is @abc.com). When John replies to the email he must select the xyz.com SMTP account when he sends the email or else his reply will go out as jdoe@abc.com.

These instructions will assume the user has administrative access to the Exchange and DNS servers on the network or is the administrator of a Microsoft Small Business Server. We will also assume the servers are running Windows 2003, Exchange 2003, and Outlook 2003 or SBS 2003. 2003 is not a requirement, but some steps will vary on other versions of SBS, Windows Server, and Outlook.

The first step in the process is to add the additional domains to the recipient policy on the Exchange server if it has not already been done. This will allow the Exchange Server to receive email sent to the additional domain(s).

  1. Open Exchange System Manager, or drill down to your Exchange instance on the Server Management Page for Small Business Server.
  2. Open Recipients and click on Recipient Policies.
  3. Right click the Default Policy and select Properties.
  4. Select the E-mail addresses tab and click New.
  5. Select SMTP address and fill in the additional domain name with the @ symbol prefix (@xyz.com) and click OK.
  6. You may modify the primary SMTP domain if desired, then click OK.
  7. Repeat for each domain you want to add.

At this point, your users can receive email sent to the additional domain only if you edit each user account and add the address for them. I recommend right clicking the Default Policy and selecting Apply this policy now. This will make the additional domain active for all users. In effect, it creates a secondary email address for all of your Exchange users in the Default Policy (normally everyone).

Now DNS needs to be setup. External DNS is provided by a wide range of providers. You will need to contact your domain host to setup the necessary record for DNS. This may be your web hosting company or the company you registered the domain with. You will want to add an A record and MX record for the outside or public IP address of your Exchange server for the additional domain. A CNAME record that aliases an existing A record is fine, or you can use an existing A record. Please contact your domain host if you need help. You can contact us at New Age Digital if you would like to change your hosting service. We can assist with all of the details. This will need to be done for all domains for which you wish to receive email.

Next we will add the domain to your internal DNS server. This will normally be your Small Business Server or PDC in a multi-server environment.

  1. Open your DNS MMC console. Normally accessed through Administrative Tools.
  2. Right click Forward Lookup Zones and select New Zone.
  3. Click Next on the New Zone Wizard and select Primary and click Next.
  4. Choose the appropriate selection on the next screen. Normally the default is correct.
  5. Enter your additional domain name (xyz.com) and click Next.
  6. Normally you will not want dynamic updates, but this may vary depending on your needs. Dynamic updates are not necessary for this setup. Click Next and Finish.
  7. Right click the domain you added and select new A record. You may need to expand the tree on the left side of the MMC console to activate the add function.
  8. Enter the prefix for the A record in the name field. This should match the A record setup on the external DNS servers for the domain. For example, if an A record, mail.xyz.com, was setup on the external DNS servers, enter mail in the name field.
  9. Type in the local IP address of your Exchange server and click Add Host. Please note that this is the internal IP address – not your outside or public IP address.
  10. Repeat for each domain that you wish to use for outgoing email.

Add a new account to each Outlook profile on each computer that will need to send email out using the new email address.

  1. In Outlook, select Tools, Email Accounts.
  2. Select View or change existing email accounts and click Next.
  3. Select Add, select POP3, and click Next.
  4. Fill in the fields on the POP3 Internet account settings screen as follows:
  5. Name . As you would like it to appear to recipients, usually the users full name.
  6. Email address – The full email address using additional domain (jdoe@xyz.com).
  7. Both POP3 and SMTP servers will be the host you setup in DNS (mail.xyz.com).
  8. The username should be the login name of the user to the domain or Exchange server (jdoe).
  9. The password is the user’s domain or Exchange password.
  10. Do not test the account settings (see below). Click Next and Finish.
  11. Make sure the Exchange account is still the default and that the user’s mailbox is the delivery location for all accounts by clicking on each account.
  12. Repeat for each outgoing address you wish to add.
  13. Repeat for each user and each Outlook profile that your users will use to send outgoing email on the additional addresses.
  14. Most Exchange servers do not have POP3 enabled by default. It does not need to be enabled, nor do we need to make any firewall or router changes to allow POP3 traffic. The next step will be to disable the POP3 half of the new account. This will negate the need to make any changes to Exchange. It will also remove conflicts with some antivirus scanners with email scanning ability, and improve the speed of retrieving new messages. Exchange is already setup to receive incoming mail on the additional domains and that email will be delivered directly to the user’s mailbox on receipt.

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