SMTP Server Setup

Posted on 2006-10-24
Last Modified: 2013-11-30
I am having problems getting SMTP working under IIS on my XP Pro machine.  I managed this successfully on another similar machine.  The SMTP server settings look very similar on both machines.
When I run blat on this machine nothing appears in the Drop or Queue folders.  It doesnt matter where I address the email message, the result is the same.

This is an SMTP email server on a local machine, not on an ISP host.  On the local machine the <Properties>, <Delivery> <Advanced> settings for the Default SMTP server shows as the Masquewrade domain and as the Fully-qualified domain name.

So I tried to telnet to on ports 23 and 25 but it failed on both cases.

What am I missing, Experts?  I am fairly dumb about this so it could be something very simple.  

Question by:TL208
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LVL 11

Expert Comment

ID: 17795008
What SMTP server are you using on your WinXP Pro machine?

Do you want to receive mail from outside? In this case do you have a public IP and hostname?
In any case, try a "telnet localhost 25" to see if your SMTP is listening
LVL 10

Expert Comment

ID: 17795164
on the xp machine run "netstat -na" and check to see that the ip address of the machine (or is listening on port 25.  If it is not, then check to be sure that the smtp service is started.  If it is, then be sure that there is no anti-virus on the machine that prevents smtp, also be sure that the windows firewall is disabled, or has exception rules to allow the smtp traffic on tcp 25.


Author Comment

ID: 17795866
ok - SMTP is started and its listening on port 25
I managed to telnet to localhost on 25
It responded with the assigned fully-qualified domain name

I then tried to follow the instructions below, but its response was "unrecognized command"

Is there some other way of testing whether SMTP is working or not?


Type telnet 25 (If you live in Canada, put 23) (where "" is the name of the smtp (outgoing) server of your email provider, such as This can be found by checking your account info in the program you normally use for email.
Type RCPT TO,,, etc.
To write the message, type DATA, followed by your message.
To end the message, put a period on a line by itself and press Enter.
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LVL 10

Assisted Solution

Sorenson earned 200 total points
ID: 17799100
The directions look good, except the canada part, port 23 is telnet, port 25 is mail, it is universal.

So.  On the PC.

Type the following:

telnet localhost 25  (wait for response)
helo (enter and wait for response)
mail (enter and wait for response)
rcpt (enter and wait for response)
DATA (enter)
now type your message  end it by putting a period on the line by itself.
this is a test message (enter)
did you get this.  (enter)
. (enter)
quit (enter)

Then see if the message goes out.  If not check the queue directories to see if it is there, and check the event log for clues.


Author Comment

ID: 17799428
After telnet localhost 25 I type:

helo (enter and wait for response)

It tells me:  500.5.3.3 Unrecognized command
LVL 11

Expert Comment

ID: 17801461
HELO should be uppercase

Author Comment

ID: 17801562
Ok - that all worked.  Except that the email was not received.  I tried several different email addresses.

I think this IP address may be being blocked by SORBS.
LVL 11

Expert Comment

ID: 17801603
Well the point is: what SMTP program are you using? Where is it supposed to deliver mail? Did you try to send (manually) an email that had to be delivered locally to your pc or sent outside?

Author Comment

ID: 17801671
I followed the instructions above and tried to telnet a message manually to an outside email address.  I also tried Blat to an outside address.  In other similar circumstances this has worked even when an IP address is blacklisted (by SORBS or others) when you send to gmail - it doesnt seem to use blacklists.  But it doesnt work in this case...
LVL 11

Expert Comment

ID: 17802242
Does Blat work?
Anyway you either have not configured SMTP properly or a firewall (yours or your provider's) is blocking the connection.
What smtp server are you using??? AFAIK winxp doesn't include one.

Author Comment

ID: 17802383
No Blat does not work.

The firewall is not enabled on this machine.

I am using the default SMTP server under IIS, which is a standard part of Win XP.
LVL 11

Accepted Solution

lbertacco earned 300 total points
ID: 17811127
Ok, then I assume that you want (at least for now) to send emails from your computer to some address out in the itnernet through your SMTP server.
This is what I'd do:
- pick a valid email address to use for testing. This should be the address of a mailbox that you can check to see if it has actually received the test emails. Let's say this address is
- then try to send an email to this address using the "telnet command"
> to do this, first you must find the hostname of the mail exchange server for
> from a command prompt type
> nslookup -"set type=MX"
> you should get a list of lines like " MX preference=5, mail exchanger =
> write down the name of one mail exhcanger with the lowest preference (say "").
> try to send an email using "telnet 25" etc... of course, when you type "RCPT TO:" you must use the test email address you have decided as in "RCPT TO:"
- see if the mail has been correctly delivered.
If not, then you have network issues (firewalls, etc)
If it worked, then there is something wrong with your SMTP server configuration (but in this case, try also sending an email to the same address but using "telnet localhost 25")

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