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451 4.4.0 Primary target IP address responded with 421 4.2.1 Unable to connect Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed

Posted on 2009-04-29
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Last Modified: 2012-05-06
Let me first run over my Exchange 07 setup. I am using an SMTP connector to send email through a 3rd party host "Network Solutions" and for incoming we are using the POP3 connectors. Our domain name is parrishconstruction.com I have set our reverse record to parrishconstruction.com. The reason for routing email through Network Solutions is that when I tried to us Exchange to send and receive email I got a poor sender base and I just seemed like there was more to know then what I did at the time. Network solutions does not support smart host or I would try that, Anyway we keep getting this error on almost every email we send which delays it for some time. It eventually makes it out but it can take as long as a couple hours to get out. Any suggestions? Should I just allow exchange to send and receive email and if so what do I need to make sure is in place to keep your sender rating from falling or becoming black listed, what should our reverse record be it we use exchange? Thanks so much for the help!
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Question by:criceparrish
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9 Comments
 
LVL 81

Expert Comment

by:arnold
ID: 24264927
Can you use your ISP's mail servers as smarthost through which you will relay?
The error suggests that the SMTP connector you have setup is unable to establish a connection.
421 is a permanent error.
Try from the command line on the exchange server to telnet networksolutionshost 25

See what it lets you do.
In your network solution setup, do you have a way to approve which IP will be sending email through them or do you have a username/password that you need to provide?  

Check the exchange logs and increase verbosity if possible to determine what the issue is.
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Author Comment

by:criceparrish
ID: 24265588
My ISP requires a user name and password for sending so I don't think I can rout the mail though them. I do not provide a user name and password for sending but I do for the POP3. I don't know about approving the IP? Network Solutions is not much help in setting this up. Do you recommend sending our mail through a third party or just using Exchange?
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LVL 81

Expert Comment

by:arnold
ID: 24265673
What issues were you seeing when exchange was doing the delivery? You could adjust the settings i.e. how many outgoing connection are initiated, how many messages can be sent through each connection etc.

See if this helps you configure your outgoing smarthost with authentication through your ISP:
http://www.arrowmail.co.uk/howto/smrthost.aspx
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Author Comment

by:criceparrish
ID: 24265878
Other then the error in the queue I did not notice anything. I have one outgoing connection I'm not sure how to tell the number of messages it can send.
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Author Comment

by:criceparrish
ID: 24266272
Based on this header can you tell what our reverse record should be? Right now is is parrishconstruction.com
Received: (qmail 4353 invoked from network); 29 Apr 2009 15:41:22 -0000
Received: from unknown (HELO p3presmtp01-19.prod.phx3.secureserver.net) ([208.109.80.168])
          (envelope-sender <crice@parrishconstruction.com>)
          by p3plsmtp03-03.prod.phx3.secureserver.net (qmail-1.03) with SMTP
          for <crice@3dadinc.com>; 29 Apr 2009 15:41:22 -0000
Received: (qmail 29138 invoked from network); 29 Apr 2009 15:41:22 -0000
Received: from parrishconstruction.com (HELO mail.parrishconstruction.com) ([207.144.53.19])
          (envelope-sender <crice@parrishconstruction.com>)
          by p3presmtp01-19.prod.phx3.secureserver.net (qmail-ldap-1.03) with SMTP
          for <crice@3dadinc.com>; 29 Apr 2009 15:41:20 -0000
Received: from SER0004.parrish.local ([fe80::101:40d6:c0de:8f24]) by
 SER0004.parrish.local ([fe80::101:40d6:c0de:8f24%10]) with mapi; Wed, 29 Apr
 2009 11:28:42 -0400
From: Craig Rice <crice@parrishconstruction.com>
To: "crice@3dadinc.com" <crice@3dadinc.com>
Date: Wed, 29 Apr 2009 11:28:41 -0400
Subject: test
Thread-Topic: test
Thread-Index: AcnI3yx/2JHDGL0xSfKcEpuk2SftIQ==
Message-ID: <C4CC8D6307B94F4792C5F3356106226D5C0AD8E933@SER0004.parrish.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
acceptlanguage: en-US
Content-Type: multipart/alternative;
      boundary="_000_C4CC8D6307B94F4792C5F3356106226D5C0AD8E933SER0004parris_"
MIME-Version: 1.0
X-Nonspam: None
Could this be causing the problem?
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LVL 81

Expert Comment

by:arnold
ID: 24266696
Your outgoing IP 207.144.53.19 resolves to remote.parrishconstruction.com and remote.parrishconstruction.com resolves to the IP so you have a matching forward and reverse.  The problem is that your greeting (helo uses mail.parrishconstruction.com)

I am not quite sure what you are pointing to.

If you provide the IP or hostname to which your server connects when it gets the 421 error, I could try and connect to see what the response is.
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Author Comment

by:criceparrish
ID: 24266743
Ok, I changed the helo to say remote.parrishconstruction.com the following is a header from an email after I changed this. From what I can tell it all looks good?

Received: (qmail 5542 invoked from network); 30 Apr 2009 03:24:08 -0000
Received: from unknown (HELO pre-smtp11-02.prod.mesa1.secureserver.net) ([10.0.19.111])
          (envelope-sender <crice@parrishconstruction.com>)
          by p3plsmtp03-01.prod.phx3.secureserver.net (qmail-1.03) with SMTP
          for <crice@3dadinc.com>; 30 Apr 2009 03:24:08 -0000
Received: (qmail 14065 invoked from network); 30 Apr 2009 03:24:08 -0000
Received: from remote.parrishconstruction.com ([207.144.53.19])
          (envelope-sender <crice@parrishconstruction.com>)
          by pre-smtp11-02.prod.mesa1.secureserver.net (qmail-ldap-1.03) with SMTP
          for <crice@3dadinc.com>; 30 Apr 2009 03:24:08 -0000
Received: from SER0004.parrish.local ([fe80::101:40d6:c0de:8f24]) by
 SER0004.parrish.local ([fe80::101:40d6:c0de:8f24%10]) with mapi; Wed, 29 Apr
 2009 23:24:06 -0400
From: Craig Rice <crice@parrishconstruction.com>
To: "crice@3dadinc.com" <crice@3dadinc.com>
Date: Wed, 29 Apr 2009 23:24:06 -0400
Subject: test
Thread-Topic: test
Thread-Index: AcnJQx4UXyf2WkaWS3isQrnn9fKsBA==
Message-ID: <C4CC8D6307B94F4792C5F3356106226D5C0AD8E9B1@SER0004.parrish.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
acceptlanguage: en-US
Content-Type: multipart/alternative;
      boundary="_000_C4CC8D6307B94F4792C5F3356106226D5C0AD8E9B1SER0004parris_"
MIME-Version: 1.0
X-Nonspam: None

The IP of the server our email is routed through is: 205.178.149.7 An example of an IP that has give the 421 error is: 143.166.224.193 (dell.com) However this error has come up with several domains, maybe even everyone we have sent to at some point.
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LVL 81

Accepted Solution

by:
arnold earned 2000 total points
ID: 24266773
Without seeing the error you were getting i.e. whether the error was reported by the remote mail server or did your server have an issue?

Check the outgoing mail log.  Increase verbosity if possible and see what is reported there.
The header seems fine.  Something else is going on.  Do you have an outgoing anti-spam mail filtering setup?
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Author Comment

by:criceparrish
ID: 24269652
Our exchange server was giving the original error I reported. Our reverse record just finally changed last night from parrishconstruction.com to remote.parrishconstruction.com I am not sure how to increase v erbosity but I did a little research and went into the registry and the RED_DWORD is set to 7? I am not sure if windows sets up an anti-spam mail filter but I have done nothing to set up anything special. However after going over all this I have noticed that we have not gotten the error today yet, with having the reverse record correct and the helo response corrected.
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