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telneting into smtp server, what reply to 'authenication required'?

Posted on 2007-12-04
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Last Modified: 2013-11-30
I'm having trouble sending email through a comcast smtp server.  Customer service has no idea where the problem lies.

So I did some reading and found that I could do some testing by connecting and sending an email through telnet.

So I connect ok, do the 'helo', the 'mail from;'  and then the server says 'authentication required'.  I don't know how to respond to that.  I tried typing in my username, expecting it would then ask for my password, but it didn't.  What does it expect from me?  How should I respond?  

Thank you,   Chris
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Question by:St_Aug_Beach_Bum
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6 Comments
 

Assisted Solution

by:billybreland
billybreland earned 400 total points
ID: 20409131
Depending on your provider settings, you should be able to use AUTH PLAIN and the response back to you will ask you for your username and password.  

Hope this helps,
Billy
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Author Comment

by:St_Aug_Beach_Bum
ID: 20409200
hmm, it just replies:

334

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LVL 1

Expert Comment

by:ankitmehra
ID: 20409512
Hey try the folloswing steps ... I guess you tried HELO instead of EHLO ..I have mentioned the proper steps to communicate to an SMTP server on Telnet.If you have any further doubts after reading the following steps, do message me or you can even browse the Microsoft KB153119.

1.  You can start a Telnet session by using the Telnet command in the following format:


telnet servername portnumber
For example, type:
telnet mail.contoso.com 25
Note You can replace servername with the IP address or the FQDN of the SMTP server that you want to connect to. Remember to press ENTER after each command.

If the command works, you receive a response from the SMTP server that is similar to the following:

220  site.contoso.com  Microsoft Exchange Internet Mail Connector  <version number of the IMC>

Note There are different versions of Microsoft SMTP or third party SMTP servers, and you may receive different responses from the receiving server. What is important is that you receive the 220 response with the FQDN of the server and the version of SMTP. Additionally, all versions of Microsoft SMTP include the term "Microsoft" in the 220 response.  



2.  Start communication by typing the following command:

EHLO test.com

Note You can use the HELO command, but EHLO is a verb that exists in the Extended SMTP verb set that is supported in all current Microsoft implementations of SMTP. It is a good idea to use EHLO, unless you believe that there is a problem with the Extended SMTP Verbs.

If the command is successful, you receive the following response:
250 OK
 

3.  Type the following command to tell the receiving SMTP server who the message is from:

MAIL FROM: Admin@test.com

Note This address can be any SMTP address that you want, but it is a good idea to consider the following issues:

a.  Some SMTP mail systems filter messages based on the MAIL FROM: address and may not permit certain IP addresses to connect or may not permit the IP address to send e-mail to the SMTP mail system if the connecting IP address does not match the domain where the SMTP mail system resides. In this example, that domain is test.com .  

b.  If you do not use a valid e-mail address when you send a message, you cannot determine if the message had a delivery problem, because the non-delivery report (NDR) cannot reach an IP address that is not valid. If you use a valid e-mail address, you receive the following response from the SMTP server:

250 OK - MAIL FROM  Admin@test.com
 
 
4.  Type the following command to tell the receiving SMTP server whom the message is to.

Note It is a good idea to always use a valid recipient SMTP address in the domain that you are sending to. For example, if you are sending to john@domain.com , you must be certain that john@domain.com exists in the domain. Otherwise, you will receive an NDR.
Type the following command with the SMTP address of the person you want to send to:

RCPT TO: User@Domain.Com

You receive the following response:
250 OK - Recipient  User@ Domain.Com
 

5.  Type the following command to tell the SMTP server that you are ready to send data:

DATA

You receive the following response: 354 Send data. End with CRLF.CRLF
 
6.  You are now ready to start typing the 822/2822 section of the message. The user will see this part of the message in their inbox. Type the following command to add a subject line:

Subject: test message

Press ENTER two times. You do not receive a response from this command.

Note The two ENTER commands comply with Request for Comments (RFC) 822 and 2822. 822 commands must be followed by a blank line.  

7.  Type the following command to add message body text:
This is a test message you will not see a response from this command.  
8.  Type a period (.) at the next blank line, and then press ENTER. You receive the following response:
250 OK
 
9.  Close the connection by typing the following command:
QUIT
You receive the following response:
221 closing connection
 
10.  Verify that the recipient received the message that you sent. If any error event messages appear in the application event log, or if there are problems receiving the message, check the configuration or the communication to the host.  


Cheers !!

Ankit
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Author Comment

by:St_Aug_Beach_Bum
ID: 20411284
Hi Ankit,

After your number 3, instead of :

250 OK - MAIL FROM  Admin@test.com

I get:

authentication required

and that's where I'm stuck... not sure what it wants.  I have checked mail (pop auth) with my email program, I don't know if that matters when doing telnet, or if pop auth is even what they are looking for?
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LVL 1

Accepted Solution

by:
ankitmehra earned 1600 total points
ID: 20411575
Hi

Can u trying doing a telnet to the localhost as in Telnet localhost 25 instead of the targeted SMTP and then try sending an email to any of the internal users.

Temme wht u get .. am waiting ...
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Author Closing Comment

by:St_Aug_Beach_Bum
ID: 31412782
Well, ended up that the problem was completely on comcast's end. Took them a week to fix it, and hours on customer service with them changing my settings over and over again, before they finally figure out it was something to do with them.  They haven't told me what.  Just one day it started working.  hmmphhfff.  They should pay me for the time I spent trying to get this to work.

Thank you both for your time, though it ended up unanswerable, I am awarding points because you put in the work.
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