SMTP Server Blues...


I'm trying to help my friend out. Their company is running Windows 2000 server and just replaced their DSL connection with a dedicated T1 line from Verizon. Earthlink has been hosting their website and continues to host their web site. They don't have an exchange server and really can't afford one.

Incoming mail from the Earthlink hosting account works fine. Their dillema is what to do for an SMTP server.

Earthlink will not allow them to send email through them, even if they authenticate, because they are connected to Verizon through the T1. Verizon will not allow them to send email through their SMTP because Verizon does not administer (host) the company's domain (That's earthlink's job).

A computer network consulting company tried to set up the Microsoft SMTP virtual server for them but all the mail just ends up in the badmail folder. Isn't this because their is no Smart Host to move the mail? Correct me if I'm wrong, but even with virtual SMTP server running, don't you still need a "real" SMTP server to talk to the mail recipient's incoming servers?

Their Windows 2000 server is behind a firewall. Is there an SMTP server available for Windows 2000 that will handle the entire process of sending mail? Is it safe and desirable to do that?

The company is non-profit and on a tight budget so I'm trying to help them resolve this in the most cost-effective way. Going to the integrated voice/data T1 with Verizon saved a lot of money but it's come at the expense of not being able to send mail!

Thank you!


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All you need is some kind of SMTP server running on your local server.  You shouldn't have to use a smart host.  What you may need to do is set up your server in DNS so remote servers can do reverse DNS lookups.  Verizon is most likely handling DNS so they should be able to help with this.  I put a couple of links below for products I found while doing a quick search.  Sorry, I don't have any experience with them.  I'd try the freebie one first.  All you need is the SMTP server, nothing else.

Here's one option for only $49:

Here's a free product:

I am surprised that Earthlink won't let you connect to their smtp server.  Infact, that doesn't make a whole lot of sense.  Then again, I'm not sure which level of service these guys have.  I work next door to a company that uses Earthlink to host their mail.  They don't use Earthlink's ISP service though.  They have a partial T1 from a local carrier.  All they had to do was configure their clients to use and put in their account and password for the smtp server.  You might want to call Earthlink back to find out what in your service agreement gives them the right to refuse access to their smtp server.  The more I think about it, the fishier this seems...

paul_lcsAuthor Commented:
Thanks Jeff,

Am I correct in saying that the Virtual SMTP server in Windows 2000 alone won't work or do you think it's just missing an MX record for reverse lookups?

Earthlink said they can buy another an email address and use that to authenticate at all the workstations. That could work, but seems crazy when they are hosting domain and email already! Authentication with their hosted email username and password doesn't work.

I'm sorry, I completely skipped over your comments about the Microsoft Virtual SMTP server.  I have never used it (seems like I have never used anything!)  FYI - you don't want to set up an MX record for your internal smtp server.  MX records are used for people delivering mail to you.  If you add one for this server, remote servers might try to contact it to deliver mail (which would really goof things up).

All you should have to do is add the server in DNS.  You would want to set up a host record "A" in your forward DNS file and a "PTR" record in your reverse DNS file.  If you use hide NAT and all of your servers appear to come from the external IP address of your firewall/router then you should just use that address for DNS.

When you say the authentication with their hosted email doesn't work, what kind of error message do you get?

paul_lcsAuthor Commented:
I was thinking the MX record would be for reverse lookups. I like your explanation, that makes sense.  The error I get with the Earthlink SMTP is:

Unable to connect to the outgoing mail server (SMTP). Please verify the server name in the outgoing mail server field.

Thanks again,

Please take a look at this link:

Is this how you have your email programs configured?

If that doesn't do the trick, please open a command prompt window (Start >> Run >> cmd.exe) and type this command:


It should return 8 different IP addresses.  They are between and  If not, then we know the problem has to do with DNS.


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