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How do you send a test email from the Windows Server command line?

The steps below require that the following requirements have been met:

  • In Windows Server, the Simple Mail Transfer Protocol Service has been installed.

  • In Windows Server, the Simple Mail Transfer Protocol Service has been set to Automatic and is listening on Port 25.

  • In Windows Server, the SMTP Virtual Server Smarthost/Outbound Security has been fully configured.  If Exchange Server is running on the Server, the SMTP Virtual Server is found within the Exchange System Manager MMC - Servers - ServerName - Protocols - SMTP.  If Exchange Server is not installed, the SMTP Virtual Server is found within the Internet Information Server MMC - ServerName - Default SMTP Virtual Server.

  • In Windows Server, the SMTP Virtual Server - SMTP Relay Restrictions have been defined.  Both the Local Loopback Address, 127.0.0.1, and the Private IP Address of the Server should be Granted access.

  • In the DNS Server which hosts the Domain, a forward and reverse entry is in place for the Server that will be sending the email.  Otherwise, receiving Mail Servers will identify sent email as spam.
  1. From the Mail Server, click Start - Run.

  2. Type: cmd

  3. Click OK.

  4. Type: telnet localhost 25

  5. Type: helo

  6. Hit Enter.

  7. Type: mail from: [address@domain.com]

  8. Hit Enter.

  9. Type: rcpt to: [address@domain.com]

  10. Hit Enter.

  11. Type: data

  12. Hit Enter.

  13. Type email text.

  14. Hit Enter.

  15. Type: .

  16. Hit Enter.
Your test email has been sent.

Please Note: When typing the above commands via telnet, you cannot hit the Backspace key.  If you do, you will have to start over from the beginning.


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