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Use Telnet to Test SMTP Communication

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Applies to: Exchange Server 2010

This topic explains how to use Telnet to test Simple Mail Transfer Protocol (SMTP) communication between messaging servers. By default, SMTP listens on port 25. If you use Telnet on port 25, you can enter the SMTP commands that are used to connect to an SMTP server and send a message exactly as if your Telnet session was an SMTP messaging server. You can see the success or failure of each step in the connection and message submission process.

Here are the scenarios where you may want to use Telnet to test SMTP communication to or from the transport servers that exist in your Microsoft Exchange Server organization:

  • Connect to your organization's Edge Transport server from a host that is located outside your perimeter network and send a test message.
  • Connect to a remote messaging server from your organization's Edge Transport server and send a test message.

The procedure in this topic shows you how to use Telnet Client, which is a component that is included with Microsoft Windows. Third-party Telnet clients may require a syntax that is different from that of the Windows Telnet component.

Prerequisites

  • Configure a Receive connector to allow anonymous access or Basic authentication   Because the message transfers that normally occur between Hub Transport servers are encrypted and authenticated, the internal Hub Transport server should have a Receive connector that is configured to allow anonymous access or Basic authentication to receive messages when using Telnet on port 25 to test communication. Anonymous access is required for Internet-facing servers

    Note

    When you send a message to a Receive connector that accepts Basic authentication, you must have a utility to convert the text strings that are used for the username and password into the Base64 format. Because the user name and password are easily discernable when Basic authentication is used, we don't recommend Basic authentication without encryption.

  • Connect to a remote messaging server   You may also want to connect to a remote messaging server from your organization's Edge Transport server. This will help to avoid rejection of the test message by Internet-facing SMTP servers that are configured to validate the source IP address, the corresponding domain name system (DNS) domain name, and the reverse lookup IP address of any Internet host that tries to send a message to the server.

  • Install and/or enable the Telnet Client   You may need to perform one or more of the following tasks before you use Telnet to test SMTP communication between messaging servers:

    • Install Telnet Client if you haven't already done so. See Install Telnet Client for details about how to install Telnet Client on Windows Vista or Windows Server 2008.
    • Enable Telnet Client on Windows Server 2008. See the procedure later in this topic.

  • Find the FQDN or IP address of an SMTP server. If you don't know the FQDN or IP address, you can use Nslookup to find the FQDN or IP address of an SMTP server. See the procedure later in this topic.

Enable Telnet Client in Windows Server 2008

Membership in the Windows Server 2008 local Administrators group, or equivalent, is the minimum required to complete this procedure.

In Windows Server 2008, Telnet Client is disabled by default. To enable it, complete the following steps:

  1. Open Server Manager.
  2. Click Action, and then select Add Features.
  3. Select Telnet Client, and then click Next.
  4. Click Install, and then click Close to complete the installation of Telnet Client.

Use Nslookup to find the FQDN or IP address of an SMTP server

To connect to a destination SMTP server by using Telnet on port 25, you must use the fully qualified domain name (FQDN) or the IP address of the SMTP server. If the FQDN or IP address is unknown, the easiest way to find this information is to use the Nslookup command-line tool to find the MX record for the destination domain.

  1. At a command prompt, type nslookup, and then press ENTER. This command opens the Nslookup session.

  2. Type set type=mx and then press ENTER.

  3. Type set timeout=20 and then press ENTER. By default, Windows DNS servers have a 15-second recursive DNS query time-out limit.

  4. Type the name of the domain for which you want to find the MX record. For example, to find the MX record for the fabrikam.com domain, type fabrikam.com., and then press ENTER.

    Note

    The trailing period ( . ) indicates a FQDN. The use of the trailing period prevents any default DNS suffixes that are configured for your network from being unintentionally added to the domain name.

    The output of the command will resemble the following:

    fabrikam.com mx preference=10, mail exchanger = mail1.fabrikam.com
fabrikam.com mx preference=20, mail exchanger = mail2.fabrikam.com
mail1.fabrikam.com internet address = 192.168.1.10
mail2 fabrikam.com internet address = 192.168.1.20

    You can use any of the host names or IP addresses that are associated with the MX records as the destination SMTP server. A lower value of preference indicates a preferred SMTP server. You can use multiple MX records and different values of preference for load balancing and fault tolerance.

  5. When you're ready to end the Nslookup session, type exit, and then press ENTER.

Note

Firewall or Internet proxy restrictions that are imposed on your organization's internal network may prevent you from using the Nslookup tool to query public DNS servers on the Internet.
MX records are not strictly required for internal message flow inside an Exchange organization. If you have to find the FQDN of any Hub Transport server or subscribed Edge Transport server in your organization, you can use the following command in the Exchange Management Shell: Get-ExchangeServer | where {$.isHubTransportServer -eq $true -or $.isEdgeServer -eq $true} | Format-List Fqdn,ServerRole
For more information, see Get-ExchangeServer and Pipelining.

Use Telnet on Port 25 to test SMTP communication

For purposes of providing an example, the following procedure uses the values that are described in the following list:

  • Destination SMTP server   mail1.fabrikam.com

  • Source domain   contoso.com

  • Sender's e-mail address   chris@contoso.com

  • Recipient's e-mail address   kate@fabrikam.com

  • Message subject   Test from Contoso

  • Message body   This is a test message

    Note

    You should always use a valid sender e-mail address so that any non-delivery report (NDR) messages that are generated by the destination SMTP server are delivered to the sender of the message.

The commands in Telnet Client are not case-sensitive. The SMTP command verbs are capitalized for clarity.

  1. At a command prompt, type telnet, and then press ENTER. This command opens the Telnet session.

  2. Type set localecho and then press ENTER. This optional command lets you view the characters as you type them. This setting may be required for some SMTP servers.

  3. Type set logfile <filename>. This optional command enables logging of the Telnet session to the specified log file. If you only specify a file name, the location of the log file is the current working directory. If you specify a path and a file name, the path must be local to the computer. Both the path and the file name that you specify must be entered in the Microsoft DOS 8.3 format. The path that you specify must already exist. If you specify a log file that doesn't exist, it will be created for you.

  4. Type open mail1.fabrikam.com 25 and then press ENTER.

    Note

    You can't use the backspace key after you have connected to the destination SMTP server within the Telnet session. If you make a mistake as you type an SMTP command, you must press ENTER and then type the command again. Unrecognized SMTP commands or syntax errors result in an error message that resembles the following:

    500 5.3.3 Unrecognized command

  5. Type EHLO contoso.com and then press ENTER.

  6. Type MAIL FROM:chris@contoso.com and then press ENTER.

  7. Type RCPT TO:kate@fabrikam.com NOTIFY=success,failure and then press ENTER. The optional NOTIFY command defines the particular delivery status notification (DSN) messages that the destination SMTP server must provide to the sender. DSN messages are defined in RFC 1891. In this case, you're requesting a DSN message for successful or failed message delivery.

  8. Type DATA and then press ENTER. You will receive a response that resembles the following:

    354 Start mail input; end with <CLRF>.<CLRF>

  9. Type Subject: Test from Contoso and then press ENTER.

  10. Press ENTER. RFC 2822 requires a blank line between the Subject: header field and the message body.

  11. Type This is a test message and then press ENTER.

  12. Press ENTER, type a period ( . ) and then press ENTER. You will receive a response that resembles the following:

    250 2.6.0 <GUID> Queued mail for delivery

  13. To disconnect from the destination SMTP server, type QUIT and then press ENTER. You will receive a response that resembles the following:

    221 2.0.0 Service closing transmission channel

  14. To close the Telnet session, type quit and then press ENTER.

Evaluate the Results of a Telnet Session

This section provides information about responses that may be provided to the following commands, which were used in the previous example:

  • Open mail1.fabrikam.com 25

  • EHLO contoso.com

  • MAIL FROM:chris@contoso.com

  • RCPT TO:kate@fabrikam.com NOTIFY=success,failure

    Note

    The 3-digit SMTP response codes that are defined in RFC 2821 are the same for all SMTP messaging servers. The text descriptions may differ slightly for some SMTP messaging servers. In the previous example, the destination computer is running Exchange Server 2010.

Open mail1.fabrikam.com 25

Successful Response   220 mail1.fabrikam.com Microsoft ESMTP MAIL Service ready at <day-date-time>

Failure Response   Connecting to mail1.fabrikam.com...Could not open connection to the host, on port 25: Connect failed

Possible Reasons for Failure

  • The destination SMTP service is unavailable.
  • There are restrictions on the destination firewall.
  • There are restrictions on the source firewall.
  • An incorrect FQDN or IP address for the destination SMTP server was specified.
  • An incorrect port number was specified.

EHLO contoso.com

Successful Response   250 mail1.fabrikam.com Hello [<sourceIPaddress>]

Failure Response   501 5.5.4 Invalid domain name

Possible Reasons for Failure   There are invalid characters in the domain name. Alternatively, there are connection restrictions on the destination SMTP server.

Note

EHLO is the Extended Simple Message Transfer Protocol (ESMTP) verb that is defined in RFC 2821. ESMTP servers can advertise their capabilities during the initial connection. These capabilities include their maximum accepted message size and their supported authentication methods. HELO is the older SMTP verb that is defined in RFC 821. Most SMTP messaging servers support ESMTP and EHLO.

MAIL FROM:chris@contoso.com

Successful Response   250 2.1.0 Sender OK

Failure Response   550 5.1.7 Invalid address

Possible Reasons for Failure   There is a syntax error in the sender's e-mail address.

Failure Response   530 5.7.1 Client was not authenticated

Possible Reasons for Failure   The destination server does not accept anonymous message submissions. You receive this error if you try to use Telnet to submit a message directly to a Hub Transport server.

RCPT TO:kate@fabrikam.com NOTIFY=success,failure

Successful Response   250 2.1.5 Recipient OK

Failure Response   550 5.1.1 User unknown

Possible Reasons for Failure   The specified recipient does not exist in the organization.