1. Type rcpt to:youremail@yourdomain.

com, and
How to Test SMTP then press ENTER.

Services Manually in The output resembles the following:

Windows Server 250 OK - Recipient <youremail@yourdomain.com>

How to Test SMTP Services 1. Type Data, and then press ENTER.

Manually in Windows Server The output resembles the following:

Summary 354 Send data. End with CRLF.CRLF

This article describes how to test the Simple Mail
Transfer Protocol (SMTP) service for any system.
Test the SMTP Service
To test the SMTP service, follow these steps:
1. On a client computer running Windows Server
or Windows 10 (with telnet client installed),
type
Telnet at a command prompt, and then press
ENTER.
2. At the telnet prompt, type set LocalEcho, press
ENTER, and then type open <machinename>
25, and then press ENTER.
1. Type Subject:This is a test, and then press
ENTER two times.
2. Type Testing, and then press ENTER.
3. Press ENTER, type a period (.), and then press
ENTER.
The output resembles the following:
250 OK
1. Type quit, and then press ENTER.
The output resembles the following:
221 Closing Port / Mail queued for delivery

The output resembles the following:

220 computername.microsoft.com ESMTP Server

(Microsoft Exchange Internet Mail Service
5.5.2651.58) ready

1. Type helo me, and then press ENTER.

The output resembles the following:

250 OK

1. Type mail from:email@domain.com, and then

press ENTER.

The output resembles the following:

250 OK - mail from <email@domain.com>

1. Install the Telnet client
Testing a connection to a mail server with Telnet can yield
valuable information when troubleshooting a mail-flow issue.
For instance, if the connection from the local server is being
denied, there will typically be a human-readable error message
displayed within the Telnet session. If the error description
doesn't provide sufficient information to troubleshoot the issue,
there will typically be an SMTP error code provided as well.
Researching this error code should provide a wealth of useful
information.
Before you can use the Telnet client to test connectivity, it
must first be installed. Below are instructions for installing the
Telnet client in Windows Server 2008 and 2008 R2.
1. Launch Server Manager.
2. In the left pane, click Features.
3. In the right pane, click Add Features.
4. Check the box labeled Telnet Client and click Next.
Note: Do not check the Telnet Server box. This
feature is used to allow other machines to connect to
this server using Telnet.
5. Click Install.
6. Once the installation is complete, click Close. It
should not be necessary to reboot the server.
For Windows Server 2012 instructions, refer to
the following Dell article and choose the Telnet
Client feature: How to Install a Role or Feature in
Windows Server 2012.
Note: While it is recommended to perform this test from a mail
server (in other words, install the Telnet client on your local
mail server and use it to connect to a remote one) in order to
closely simulate real-world email delivery, it is also possible to
install the Telnet client on a Windows client OS, such as
Windows 7, by using the Programs and Features Control Panel
applet.
2. Test the connection and send an email
Once the Telnet client has been installed, follow the steps
below to test email delivery.
1. Open a command prompt.
2. Type the following command: telnet <mail server
name or IP> 25
o You should receive output similar to the
following:
220 remote.mailserveraddress.com ESMTP
NOTE: Once the telnet session is established,
the Backspace and Delete keys do not work. If
a typo is made, press Enter and retry the
command. In some cases, it may be necessary
to close the telnet session and reconnect.
o If you receive an error similar to Could not open
connection to the host, on port 25: Connect failed,
this indicates that your machine could not establish a
telnet session with the destination server using port 25.
If you initially attempted to connect using the
destination server's name, try to connect using its IP
address instead. If this is successful, you likely have a
DNS issue. If you are unable to connect using the
destination server's name or IP address, port 25 is
being blocked somewhere between your machine and
the destination server. The issue is probably due to a
firewall on the destination server's end, but it can also
be caused by a network misconfiguration or firewall
on your end.
o If you receive output similar to the following:
554-remote.mailserveraddress.com
554 Your connection has been blocked due to low
sender reputation...
Connection to host lost.
The public IP address associated with your mail server
has developed a bad reputation. If you recently
acquired this IP address, its previous owner likely sent
spam from it, and your best option may be to request a
different address from your ISP. If this is not feasible,
there are other options, but there is not always a quick
or easy solution to this issue. The error message may
include additional instructions for resolving the issue.
If not, this blog entry has a number of suggestions.
Unfortunately, it may simply be a matter of waiting for
your address's reputation to improve, and this can take
considerable time.
3. Type: EHLO <mail server internet name>
Replace <mail server internet name> with your mail
server's public fully qualified domain name - for
instance, mail.dell.com.
4. Type: mail
from: <your_name@yourdomain.com> and press
Enter.
5. Type: rcpt to: <recipient@recipientdomain.com> and
press Enter.
6. Type: data and press Enter.
7. Type: Subject: <a subject here> and press Enter.
8. Type: This is a test message sent from telnet. and press
Enter.
9. Type: . and press Enter
The message should be accepted for delivery.
Setup and Configure configure Microsoft Exchange Server for
that purpose. If you are looking a free mail
server then I recommend hMailServer.
SMTP Server on
Windows Server 2008 Installing the SMTP
R2 feature
April 26, 2012 by japinator
1. Click Start > Run and then
enter servermanager.msc in
There has been some confusion about how the Open dialogue box then click OK to
to setup and configure an SMTP load Server Manager:
Server or mail relay on Windows Server
2008 R2. The confusion has arisen due to
C:\Users\Admin>servermanager.msc
the SMTP server component not being
managed from with IIS 7.5 but is instead 2. Use the Add Features Wizard to
managed from the IIS 6 console. In order to select SMTP Server on the Select
have SMTP working you must install IIS 6 as Features page. To initiate this, right-click
a feature. The following steps will explain on Features and click Add Feature:
how to setup and configure SMTP from start
to finish.

Note: The steps for installing an SMTP

Server or mail relay on Windows Server
2012 are very similar except for a few minor
GUI changes. See this post for the exact
steps.

I have noticed a few forum posts where

people are wrongly following the steps in
this article thinking that they are setting up a
mail server to send and receive emails for
their domain – this is incorrect. The steps
outlined in this post are to create a virtual
SMTP Server or mail relay, which sends
messages only. This is typically used when
web applications generate emails and
use the mail relay to deliver them. That is
very different from setting up a mail server. If
the latter is your desired goal and it is for a
commercial operation, then I suggest you
search online for steps to install and
3. In the Features section check SMTP
Server and click Next:

4. You may see a dialogue box like the one

below stating that certain role services and
features are required for SMTP:
5. Click Add Required Role Services and
then you will return to the
previous Features section. Ensure SMTP
Server is checked then click Next.

6. In the Web Server (IIS) section,

click Next to proceed to the Role
Services section:

7. The Role Services should be pre-

populated – IIS 6 Management
Compatibility should be selected, and
below it, IIS 6 Metabase
Compatibility and IIS 6 Management
Console should also be checked.
Click Next to continue:
8. In the Confirmation section click Install: 9. In the Results section click Close to
complete the installation of the SMTP
Server:
 11. In IIS 6 Manager right-click on SMTP
Server and select Properties:

12. In the General tab, unless you want

the SMTP Server to use a specific IP
address, leave the settings as they are so
Configuring the SMTP that the IP address is set to (All
Unassigned):
Server
The next step is to configure SMTP. To do
so we will need to open Internet
Information Services (IIS) Manager 6.

10. Click Start > Run and then

enter inetmgr6 in the dialogue box then
click OK to load IIS Manager 6.
13. To proceed, click on the Access tab: 14. Click on the Authentication button and
ensure Anonymous access is checked and
then click OK:
 The Connection setting controls
which computers can connect to the SMTP
server and send mail. By granting
only localhost (127.0.0.1) access, limits only
the server itself the ability to connect to the
SMTP server. This is a requirement for
security.

16. Click OK to return to the Access tab and

then click on
the Relay button. Enter 127.0.0.1 as the IP
addess and then click OK:

15. Once back in the Access tab, click on

the Connection button. Select Only the list
below and then
click Add. Enter 127.0.0.1 as the IP addess
and then click OK:

The Relay section determines which

computers can relay mail through this SMTP
server. By only allowing the localhost IP
address (127.0.0.1) relay permissions it
means that only the server itself can relay
mail. Conversely, it prevents the SMTP
server from being an open relay and being
used to send unsolicited spam email by
other computers on the internet, which could
lead to the SMTP server being blacklisted.

17. Next, go to the Messages tab. Here you

can enter an email address where copies of
non-delivery reports are sent to. You can
also configure the location of
the Badmail director, however, the default
setting should suffice:

19. Click on the Outbound Security button

and ensure Anonymous access is
selected. As the only server that can
connect and relay mail through the SMTP
server is localhost this security settings is
fine:

18. Next, go to the Delivery tab:


20. Click OK to return to the Delivery tab
and then click on Outbound Connections.
Leave the defaults as they are:
21. Click OK to return to the Delivery tab
and then click on Outbound Connections,
then click on the Advanced button:
Here you will need to enter the fully-qualified
domain name of the SMTP server. This will
be the host name or A record that has been
created in your DNS zone file. This is
straight-forward to do but you will have to
confirm how you do this with the party that
manages DNS for your domain. I have
entered mail.vsysad.com as this is fully-
qualified. If you click on the Check
DNS button you can confirm whether your
chosen name resolves successfully. In my
case it does as I see the following:
 22. Click OK and then OK again to exit
the SMTP Virtual Server Properties.
You can also perform this test by
running nslookup to confirm the existence
of the host name as well as confirming the
IP address it resolves to – which should be
the IP address of your server:
Please note that DNS is crucial to
successful email delivery. If your SMTP
server cannot resolve the domains it is trying
to send messages to then it will fail. Ensure
that the DNS servers you have configured
are able to resolve DNS queries
successfully. From the above screenshot
you can see that the DNS server I have
configured, cachens2.dfw1.rackspace.co
m, was able to successfully resolve my
SMTP server’s
hostname, mail.vsysad.com. This is one of
Rackspace’s many DNS servers and I am
100% confident it works fine.
The reason I am highlighting this is because
if your SMTP Server sits within a corporate
network it will most likely use an internal
DNS server. Often these are only configured
to resolve internal namespaces therefore
resolving external hostnames may fail. Also,
firewall rules may block your SMTP Server
from querying any DNS servers so please
check and ensure DNS queries are resolved
successfully and if not make sure it get
fixed before going onto the testing phase
below.
Another very important point about DNS is
that you must ensure that you have a PTR
record for reverse DNS lookups configured.
The PTR record allows your SMTP Server’s
public IP address to be resolved back to
your hostname. Some of the big email
service providers perform reverse DNS
lookups of mail servers connecting to them
as a security measure to check their
credibility or reputation. Your web hosting
company should have a control panel that
allows you to configure reverse DNS if you
have a dedicated public IP address. Not
having a PTR record will not guarantee
email delivery failure but it will very likely
delay email delivery and at worst may result
in your messages being blocked and your
host being blacklisted. I highly recommend
you you configure a PTR record for your
server.
Follow the instructions in this post which
shows you how to verify correct DNS
configuration using the SMTPDIAG tool.
23. The last configuration step will be to set
the SMTP Service to Automatic so that it
automatically starts when the server boots
up. Open up the command prompt and run
the command below to enable this setting:
C:\Users\Admin>sc config "smtpsvc" start=
auto
[SC] ChangeServiceConfig SUCCESS
Then run the command below to confirm
that the service is actually running:
C:\Users\Admin>sc query "SMTPSVC" | find
"RUNNING"
STATE : 4 RUNNING
If the SMTP Service is not running the
command above will not return a
state/result. If that is the case then run the
command below to start it:
C:\Users\Admin>net start smtpsvc
The Simple Mail Transfer Protocol (SMTP)
service is starting.
The Simple Mail Transfer Protocol (SMTP)
service was started successfully.
We are now ready to test the configuration.
Testing the SMTP
Server
The next step is to verify that the SMTP
server is able to send email successfully. To
do this follow the steps below:
24. Create a text file on your desktop
called email.txt and paste the following into
it, remembering to change the email address
information to reflect your own details:
From: blog@yourdomain.com
To: email@yourdomain.com
Subject: Email test
This is the test body of the email
.
25. Save the changes to email.txt and then
copy the file to C:\inetpub\mailroot\Pickup.
The SMTP server monitors this folder and
when it detects the email.txt file, it will read
the contents and send the email to the
address in the To: section. This should
happen almost immediately.
26. Check the email address the email was
sent to and it should arrive shortly – the
email was sent to my Gmail account:
An alternative way of doing this is to use a
script to perform the same email test. Simply
save the code below into a file
called email.vbs, remembering to change
the email address information to reflect your
own details:
Dim sch, cdoConfig, cdoMessage
sch
= "http://schemas.microsoft.com/cdo/configur
ation/"
Set cdoConfig =
CreateObject("CDO.Configuration")
With cdoConfig.Fields
.Item(sch & "sendusing") = 1 '
cdoSendUsingPort
.Item(sch & "smtpserver") = "127.0.0.1"
' .Item(sch & "smtpserverport") = 25
.update
End With
Set cdoMessage = CreateObject("CDO.Message")
With cdoMessage
Set .Configuration = cdoConfig
.From = "blog@yourdomain.com"
.To = "email@yourdomain.com"
.Subject = "Email test"
.TextBody = "This is the test body of the
email"
'.AddAttachment "c:\images\myimage.jpg"
.Send
End With
Set cdoMessage = Nothing
Set cdoConfig = Nothing
MsgBox "Email Sent"
Once the file has been saved to the desktop
double-click on it and it should automatically
send the the email. A message box pops up
to confirm that the email was sent:
as info@yourdomain.com that monitor this
information. See this post to learn how to do
this using an ASP.NET 4.0 C# email web
form application.
That’s all there is to it! Now you have a fully
functioning STMP server that can
successfully send emails. Many of the
companies that I have worked with use this
method to send emails generated by
their web applications.
If emails are not being successfully
delivered you may notice that messages are
building up in specific SMTP folders. Visit
this post to understand the purpose of each
SMTP folder and how to approach issues
when messages are queuing up in those
folders.

Apparently there’s more than one way to

skin a cat, there’s also more ways to test
your mail relay server:

You can also use telnet and PowerShell to

test mail sending/routing via SMTP Server.
Please refer to this post to see how to do
this.

You can also use an email web form

application which is similar to a contact
us page on a website which allows you to
post some feedback, which then uses an
SMTP Server to deliver the messages to
specific email contacts such