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I get 530.5.7.1 Client was not authenticated message telnet

Posted on 2011-04-30
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Last Modified: 2012-05-11
I get 530.5.7.1 Client was not authenticated message when trying to connect from telnet terminal
it is a microsft esmtp mail service - exchange server.
my hostname : vvv.cxb.com  Port : 25
typed ehlo
and it provides me with
250-ail-EXC09-01.abc.cdef.org Hello [9.6.167.12]
250-SIZE
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-AUTH NTLM
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250-XEXCH50
250-XRDST
250 XSHADOW

I want to send a sample mail through the telnet - i get 530.5.7.1 Client was not authenticated message after entering the mail from : <abc@def.com>
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Question by:joseph301074
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Expert Comment

by:robertkennedy
ID: 35497007
It sounds like the mail relay you are connecting to is not configured to accempt messages from unauthenticated users or has restrictions configured to only accept messages from certain IP addresses.

I would start by firing up the Exchange management console and checking the configuration of the relay. The event logs on the exchange hub transport server which hosts the relay shoudl also be able to provide more insight into what is causing this error.
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Author Comment

by:joseph301074
ID: 35497097
they are configured to accept messages from authenticated users. how can i send in the authenticated info on the telnet terminal ?
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Expert Comment

by:robertkennedy
ID: 35497373
Connect to the SMTP Server
C:>telnet <SMTP Server name or IP> 25

If the connection is successful you should receive the SMTP Server banner. It should look something like this and return the 220 code on the first line.

220 SMTPServer.testdomain.local Microsoft ESMTP MAIL Service ready at Sat, 8 Jan 21
10 6:03:15 –0600

If you receive output, try saying hello to the server with the ‘ehlo’ command.  After you press ENTER you should receive a list of available options on that particular SMTP server.  Take note of the line that reads ‘250-AUTH NTLM LOGIN’.  If you want to test authenticated SMTP, you need to have the ‘AUTH LOGIN’ command available.  AUTH LOGIN translates to basic authentication.  For instance, this server supports both NTLM and basic authentication.

ehlo
250-SMTPServer.testdomain.local Hello [192.168.127.10]
250-SIZE
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-AUTH NTLM LOGIN
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250-XEXCH50
250 XRDST

If you don’t see the option for ‘AUTH LOGIN’ check your SMTP server settings.  In Exchange 2007, you can open the Exchange management console, browse to Server Configuration, select Hub Transport, and then check the properties of the default receive connector.  In particular, check the authentication tab.

Make sure the basic authentication is selected.  Also ensure that the check box beneath basic authentication (Offer Basic authentication only after starting TLS) is unchecked.  If it’s checked you probably won’t get the ‘AUTH LOGIN’ option.

Once we have basic authentication configured we can try sending a email.

Login to the STP Server
AUTH LOGIN
334 VXNlcm5hbWU6

It’s important to note here that authentication in SMTP is done using Base64 encoded phrases.  So when I enter ‘AUTH LOGIN’ and press enter the server returns ‘VXNlcm5hbWU6’ which is Base64 for Username:.  Any and all parts of the authentication discussion will be in Base64.  I use this web site…

http://www.webpan.com/Customers/Email/base64_conversion.htm

to do Base64 encodes and decodes.  You can Google for a different method if you prefer.  Let’s do the entire authentication conversation in Base64 and then I’ll show the translated input and output.

Conversation in Base64
AUTH LOGIN
334 VXNlcm5hbWU6
YWRtaW5pc3RyYXRvcg==
334 UGFzc3dvcmQ6
cGFzc3dvcmQ=
235 2.7.0 Authentication successful

Translated back to plain text
AUTH LOGIN
334 Username:
administrator
334 Password:
password
235 2.7.0 Authentication successful

Once we receive the authentication successful response we can test sending a email as that particular user.  This is no different then sending a test email through telnet without the authentication piece.

Send the test email
mail from:administrator@testdomain.com
250 2.1.0 Sender OK
rcpt to:user@mydomain.com
250 2.1.5 Recipient OK
data
354 Start mail input; end with <CRLF>.<CRLF>
This is a test email
.
250 2.6.0 <4b5125d60-e494-47f2-9917-7bd91e455544@SMTPServer.testdomain.local> Queued
mail for delivery

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Author Comment

by:joseph301074
ID: 35503278
typing 'AUTH LOGIN' gives me unreognized authentication type.

" In Exchange 2007, you can open the Exchange management console, browse to Server Configuration, select Hub Transport, and then check the properties of the default receive connector.  In particular, check the authentication tab."

can i do this from my XP desktop  having the exchange server  management console installed and having only  user access rights to my exchange server ? Thanks.



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Accepted Solution

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robertkennedy earned 2000 total points
ID: 35503580
I believe you require a higher level of administration rights to Exchange. I have only tried with Exchange server administrator rights. Launching the console from your computer should not matter provided you have sufficient rights to Exchange.
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