CIO Forum: Members solve an e-mail dilemma

Ask tech pros where they turn for the best insight on a tech glitch when time is short, and most will tell you that they seek the advice of a colleague or network of peers. That's exactly where one CIO member got the answer to a puzzling e-mail dilemma.

Welcome to CIO Forum—where tech leaders get real help and insight from colleagues. If you have a question for which you can't seem to find an answer, send it in to CIO Republic, and we’ll find an answer, or two, for you.

The dilemma
We have one Exchange server on our network that receives mail that is relayed via our ISP. Our ISP also has 20 POP3 e-mail boxes for our regional offices that only have one worker. We only have a 56K permanent dial-up connection at all offices, including the head office. The problem I have is that when we try and send an e-mail to the regional e-mails [addresses] from inside the Exchange network, we get failed mail. Is there any way to set up Exchange to forward mail to e-mail addresses with the same domain name that are POP3 boxes not hosted on our internal server?

The responses
The response to this technical call for help by CIO members was tremendous, so we’re providing several solutions. All the respondents below are the proud recipients of a TechRepublic mug.

Solution 1
If the POP3 e-mail is within the same domain, it can be set up with a site connector. Exchange does POP3 very easily, and the e-mail addresses for the POP3 site can even be added onto the Exchange server so that the addresses will be recognized.

—Mike Emig

Solution 2
Easy—create external e-mail addresses through Exchange Administrator. These can also be seen in the GAL.

—Deborah Iversen

Solution 3
Here's what I do all the time on Exchange 5.5, so it will probably work the same way on 2000:
  1. Create a subdomain for the POP mailboxes at the ISP (i.e.,
  2. Configure two mailboxes for each user: On the Exchange server, configure, and at the ISP, configure Also, configure a global mailbox on the Exchange server for an Internet address (
    You only need this global box because Exchange 5.5 requires a mailbox to configure forwarding—you just can't type an Internet address.
  3. In Exchange Administrator, configure forwarding for the mailbox so that it is forwarded to the global account After you configure the forwarding, you can hide the Global box so that it doesn't appear on the GAL.
  4. At the mail client, configure the reply address to be (thereby hiding the subdomain from the public).
  5. Set up an MX record in the DNS for the subdomain to point to the ISP mail server. You'll also have to tell the ISP you're doing this so that they can configure their POP mail server properly.

If all this is set up properly, mail received at the Exchange server is forwarded to the POP mailboxes and can then be picked up by the remote users.

—Rick Dexter, MCSE

Solution 4
I’m not sure of the absolute answer to the question; however, we have had problems before where the Exchange server literally changed the POP3 e-mail address to a global (internal) address. I surmise that the Exchange server recognized the reference? We’ve never quite established why this happened. It also would change the e-mail address entered into Vcards sent through Outlook to the same internal address.

My suggested workaround would be to establish an outside dummy mailbox on the server at your ISP that would be an automatic forwarder for internal messages to the correct POP3 account (example: forwards to

L.R. Birk

Solution 5
I recently had a client trying to solve a virtually identical issue, and here's the solution we implemented:
  1. Changed the dial-up line at the main office to a DSL connection with a static IP and DSL router. Any broadband solution will do. (Cost: $90/month)
  2. Had all of the POP3 accounts at the ISP moved to the local Exchange server. They will refer to this as "redirecting the MMX records." Basically, any mail traffic to the ISP is routed to your public IP. (Cost: $0)
  3. You will have to open ports to allow SMTP, TCP/UDP, and VPN traffic on the DSL router. The documentation provided with your router can walk you through it, as can your ISP. (Cost: $0)
  4. You will need to turn on VPN services on your PDC and set up your DSL router to pass all VPN requests to the IP address of the internal server. This is great because the private IP is not exposed outside the firewall, and you can still have a cost-effective and secure remote-access solution. (Cost: $0)
  5. Walk your remote users through setting up a VPN connection and changing their mail settings. (Cost: a little long distance and some aggravation from your remote users)

Total effort=1 day

  • All remote clients can create a VPN connection (using their existing dial-up accounts) to connect and share files (in addition to e-mail) on a secure connection.
  • Full user control over the e-mail accounts—naming conventions, aliases, and security.
  • For collaboration purposes, remote users can share calendars and public folders.
  • Backup: Remote users can synchronize mail to the Exchange server, creating duplicate storage of their messages. I'd bet right now that if a remote user's computer died, all of their e-mail would be gone too. Am I right?

David Hutchison

Solution 6
The easiest way to perform this task is as follows (this assumes a Win2K implementation with Active Directory):
  1. In the directory, create a container to hold all of the forwarding accounts. (This is a housekeeping recommendation only.)
  2. Create the 20 users using the Contact object (right-click New Contact) with an easy-to-recognize identifier in the name (for instance, userabc_forward).
  3. For the e-mail address of the newly created contact, put the POP mail address of the corresponding user account.
  4. Turn off the Automatically Modify E-mail Addresses Using The Recipient Policy option on the E-mail Addresses tab.
  5. Save the contact and repeat the same steps for the other users.
  6. Open the user's normal account properties in AD and select the Exchange General tab.
  7. Click Delivery Options and put in the forwarding contact name for this account (for instance, "userabc" forwards to "userabc_forward").
  8. If desired, click the option to deliver mail to both the normal Exchange account and the forwarding account.

What does this do? When e-mail arrives in Exchange via the Internet or via an internally sent message, Exchange determines that a forwarding account is in place. The e-mail is then sent to the forwarding account based on the "contact" e-mail address properties. This works well, as the users maintain their "normal" Internet mail address when receiving mail. The only "gotcha" with this method is that when they reply, their e-mail will be sent out via the POP accounts as well. If those POP mail accounts do not share the same domain name as the Exchange server, users will not be able to set their reply address to match their corporate identity. If they do, many servers will reject their messages as having been relayed.

—Eric Burke

Can you solve this member’s problem?
Below is a question that another TechRepublic member sent in to CIO Forum. If you can provide an answer, which we’ll publish on the site along with the question next week, we’ll send you a TechRepublic coffee mug or a T-shirt!

The dilemma
At our company, we have individual licenses for every piece of software that is installed; moreover, we have purchased everything we have from an accredited distributor. However, a lot of our computers came preinstalled with OEM software. In addition, they also come with a software package with legitimate licensing materials and manuals. Because of this, not all of the computers correspond to each license (registration #). Would we be in violation of any laws?

Furthermore, various help desk technicians have used the same copy to troubleshoot or reinstall software. Therefore, some of the computers may have the same copy installed (i.e., MS Office). Is this a problem even if we have the accounted licenses for those computers? (We have a legally purchased copy with a license for every computer.)

Share your knowledge with colleagues
If you have an answer to this member's question, send it in, and if we feature it in our next CIO Forum, you’ll get a TechRepublic mug or T-shirt.


Editor's Picks

Free Newsletters, In your Inbox