Sendmail SMTP errors

Hello,

When attempting to send an email to any user who utilizes Office 365, we are receiving the below bound back.   I can telnet to the theirdomain.mail.protection.outlook.com from the sending server.   Also included is the sendmail log

Jan 27 10:54:41 ourserver sendmail[9221]: s0RFsejc009221: to=auser@ourdomain.com, delay=00:00:01, xdelay=00:00:01, mailer=esmtp, pri=125676, relay=mail.ourdomain.com. [192.168.50.20], dsn=2.0.0, stat=Sent (<201401271554.s0RFsejc009221@ourdomain.com> [InternalId=17068806] Queued mail for delivery)

Jan 27 10:54:41 ourserver sendmail[9221]: s0RFrjjc009217: s0RFsejd009221: postmaster notify: Host unknown (Name server: theirdomain.mail.protection.outlook.com.: host not found)


Delivery has failed to these recipients or groups:

auser@theirdomain.com
The recipient's e-mail address isn't correct. Please check the e-mail address and try to resend the message. If the problem continues, please contact your helpdesk.



The following organization rejected your message: theirdomain.mail.protection.outlook.com.







Diagnostic information for administrators:

Generating server: server.ourdomain.com

auser@theirdomain.com
theirdomain.mail.protection.outlook.com #<theirdomain.mail.protection.outlook.com #5.1.2> #SMTP#

Original message headers:

Return-Path: <user@ourdomain.com>
Received: from localhost (localhost [127.0.0.1])
      by server.ourdomain.com (8.13.4/8.13.4/SuSE Linux 0.7) with SMTP id s0RFrjjc009217;
      Mon, 27 Jan 2014 10:53:48 -0500
Message-ID: <201401271553.s0RFrjjc009217@ourdomain.com>
X-Mailer: SQL
Date: Mon, 27 Jan 2014 10:53:45 -0500
To: auser@theirdomain.com
From: "A User" <auser@ourdomain.com>
Subject: So and So
Reply-To: "Another User" <anotheruser@ourdomain.com>
MIME-Version: 1.0
Content-Type: text/plain
Status: O
silvercasAsked:
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silvercasConnect With a Mentor Author Commented:
Since office 365 offered free accounts for 30 days, I created an account.  This account didnt exhibit any issues.  I reached out to Office 365 and tested with their account and we didnt experience any issues.  Unfortunately the office 365 team was unable to help me with the domains we are having issue with.  To get help with those domains I would need to contact the office 365 admin for the troubled domains, which has proven to be difficult.
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nociSoftware EngineerCommented:
Is this actualy correct? theirdomain.mail.protection.outlook.com

Try to lookup the MX record from theirdomain.comand and if that is missing the A or AAAA record, and go from there. Something hasn't been setup correctly.
Obviously without actual names we can;t do that for you.
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SandyCommented:
recipient doesn't exist .. that's what i think

TY/SA
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silvercasAuthor Commented:
noci:  theirdomain was changed to protect the innocent.  they have mx recrords

sandeep_agarwal : recipient exist as I can email them from another system
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nociSoftware EngineerCommented:
well your DNS cannot translate the name for you or is unable to find another server that can do it. That's what the error means.

Have you tried:
telnet  theirdomain.mail.protection.outlook.com 25

(You can exit with QUIT, enter).

that is what sendmail also attempts to do.
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silvercasAuthor Commented:
noci: did this test and it works find from the server.
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SandyCommented:
Try below

#dig @dnsip mx
theirdomain.mail.protection.outlook.com

If no output then its a dns issue.

TY/SA
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silvercasAuthor Commented:
dig @<ip of dns server> mx theirdomain.com

works fine and returns mx records

it appears that sendmail has an option to watch what it does to a message.  can this test be done with keeping sendmail up?
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arnoldCommented:
Use telnet on your system
after you lookup the MX.
Establish a connection to one of the listed records starting from the one with the highest preference (lowest number).
see what response you get
telnet
set localecho
open MX_RECORD 25

ehlo yourhostname
mail from: <youremailaddress@yourdomain.com>
rcpt to: <user@theirdomain.com>
data
From: <youremailaddress@yourdomain.com>
To: <user@theirdomain.com>
Subject: testing

Message body
.
to every command up until data you should receive a 2xx message.  To data you should receive a 354 response.
To the ending single period on the line you should receive a 2xx with a notice that the message was accepted and queued.  If you get any other message, it should tell you what is going on.


In the example you posted, it seems that theirdomain is not longer served by the provider or they have a DNS error such that periodically the host does not resolve.
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arnoldCommented:
Unfortunately, without information on the underlying domain, you are the eyes. What was the conclusion of the suggested test where you will replicate an SMTP session to the "troubled" domain.

The troubled domain might no longer be hosted by 365.

host not found means your system can not get an IP for the theirdomain.mail.protection.outlook.com
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arnoldCommented:
A mixed solutions suggests that some of the comments you received help in resolving your question.
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silvercasAuthor Commented:
mixed solution
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