troubleshooting Question

Using POP3 in conjusction with Exchange

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Headhunting55 asked on
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Hi, Experts;

I have a scenario in front of me for which I need some advice.

Here’s the infrastructure setup:

SBS 2003 Standard

Everything is pretty plain Vanilla in this environment EXCEPT that rather than have the exchange server handle all incoming and outgoing email, we have an outside POP3 server provided by our Web Hosting Company for INCOMING mail. (Again, I inherited this environment….I intend to bring it all in-house in January). All of our incoming mail is delivered, of course, through the POP3 server. We have about 20-25 users.

Let’s say that the company is called

In addition to the full-time employees, the Client employs a number of independent contractors (ICs) that work from their homes…..they do not come into the office, therefore they do not need an account on our network. The Client wants them, however, to have a email address to use when they correspond with my Clients’ clients.

For instance, Kelly is an IC, so my client wants her to have the email address of

Now, this would appear to be a fairly simple task:  We simply setup a POP3 account for the IC on our Web Host’s POP3 server the same way we do for employees. The IC sets up Outlook at home using our POP3 mailserver (, and uses their own ISP for outgoing SMTP.

I have already set this up for an IC, and it appears to work very well. I have sent mail TO the IC from my home account, from the Client’s Network to the IC, I’ve done replies, added attachments, most everything I could to simulate a production environment. It all APPEARS to work FINE.

Here’s the problem:   the Client doesn’t think it will work in the long run. According to the Client, My predecessor tried setting up the same thing a couple of years ago on the same network, and while it worked part of the time, the Client said that emails began to disappear, so they changed to using Hotmail for all IC accounts. The Client contacted my Predecessor this morning to verify this, and he states that there was indeed a problem. He said that “unless JOEBLOW hosts their own mail, if an IC sends a piece of mail it never leaves the organization unless they log onto our server to use the mail (which we didn’t want to do).”

I know, that doesn’t make a whole lot of sense, but that was his email reply.

Therefore, my question to all of you is:  Is there anything here I’m missing?  Can anyone here think of a scenario where emails would be missing in a configuration like this?
I’m having a problem convincing the Client to go forward with this arrangement, because the former IT Consultant is adamant about it not being a functional solution.

Help me out!

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