Master Exchange 2007

powershell, automation & more…

Basic SMTP Telnet test exchange 2007 send connector send port 25

Posted by shauncroucher on October 26, 2009


This test is designed to TEST ‘outbound’ mail. That is, mail that you are trying to send to external recipients from your organisation. It is important to run this test from the Exchange server if possible to mimick the steps your exchange server goes through as accurately as possible.
 
Note you cannot use backspace or delete when using telnet, if you make a spelling mistake, start the command again after the error is generated.
 
Note you should use < > around email addresses as some email servers will not accept email addresses unless they are enclosed in <   >
 
Step 1

Use mxtoolbox.com to find the MX record of the mail server you wish to test.

So to find the mailserver accepting email  for bbc.co.uk, type bbc.co.uk in the MX Lookup box.
make a note of the hostname (or one of the multiple hostnames) returned as we need this for Step 2.
Step 2

Note: If you are using Vista or Windows 2008 telnet is not enabled by default. See this excellent article on petri http://www.petri.co.il/enabling-telnet-client-in-windows-server-2008-and-windows-vista.htm for details on how to enable Telnt on Vista or Windows 2008.  

Log onto your Exchange server and open up a command prompt.

Type the following:
 
telnet [HOSTNAME RETRIEVED IN STEP 1] 25
[Wait for 220 response]
 
EHLO [YOUR_DOMAIN_NAME_HERE]
[Wait for 250 response]
 
MAIL FROM:<ONE_OF_YOUR_ORGANISATION_EMAIL_ADDRESSES>
[Wait for 250 response]
 
RCPT TO:<[A_VALID_EMAIL_ADDRESS@THEIR_DOMAIN_NAME]>
[Wait for 250 response]

DATA
[Wait for 354 response]
This is a test message
.
(note the dot on its own to end the session)
 
You should now get a message that the email has been queued for delivery.

Screenshot of how this conversation should look:

Screeshot Telnet Windows SMTP test

Screenshot of a telnet session to a server and submit SMTP message

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