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EHLO with a 500

I have been getting the following error somewhat often at random. Sometimes the message goes through fine and others it bounces back with this message in the event log:

A non-delivery report with a status code of 5.5.0 was generated for recipient rfc822;3167067121@vtext.com (Message-ID <D73E0A372BFF1343824ECF7F87F87929010F0D30@exchange02.corp.plazare.com>).  
Cause:  This message indicates a generic protocol error (SMTP error).  For example, the remote SMTP responds to an issued EHLO with a 500 level error and the sending system will QUIT the connection and report this with NDR indicating the remote SMTP server canÆt handle the protocol.    
Solution:  View the SMTP log or run a netmon trace to see why the remote SMTP server rejects the protocol request.
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dpickard
Asked:
dpickard
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1 Solution
 
SembeeCommented:
Not really enough on there to go on.
Any pattern with the domains listed?

That would tend to indicate an SMTP delivery issue, there are various causes, but difficult to pinpoint what.

Simon.

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dpickardAuthor Commented:
They are typically to text message accounts like vtext.com and sometimes to free webmail accounts. I can send the exact same message twice and one will bounce and the other wont. The only recent change I had was a reenabled 8bit Mime which I had turned off in exchange.
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SembeeCommented:
Unfortunately still not enough to say what the issue is.
Large email providers will often have clusters of email servers, so it could be a problem with one of those. However if it is happening with more than one domain and they aren't using the same email servers the problem is probably closer to home. Firewall, av and antispam are the usual causes of SMTP delivery issues.

Simon

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dpickardAuthor Commented:
I have been having it randomly happen with differnent prioviders so I do beleive it is on my end. My mail has a long trip to get to my users box unfortunatly. It comes in on a PIX 506e goes to my barracuda spam firewall then to the exchange server where it is subjected to trend micro. I have turned of trend micro from scanning for spam but there is not way to keep it from scanning email for viruses or at least that I have seen. After all that if it makes it through it is sent on to the user, Outgoing mail however is sent directly from the exchange server and I would imagine that trend micro scans outgoing messages for viruses aswell. I received a few more of these last night to a wide range of other providers including cox.net which is a major ISP in my area. The bounced message that is received in the user box is:

There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
            <mail.plazare.com #5.5.0 smtp;550 SMTP connection refused>
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SembeeCommented:
That last message means what it says - the receiving server rejected your message. It doesn't say why, but it could be blacklisting, wrong DNS settings, something like that.

Ensure that the PIX has fixup SMTP disabled as that can cause problems.

Simon.

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dpickardAuthor Commented:
I double checked to make sure that the fixup SMTP was still diabled I also tried uninstalling trend from the exchange server temporarily. I also checked to make sure I was not on any blacklists via www.dnsstuff.com. I added another dns servers in my dns servers list and moved them to the top because I am not impresses with my ISPs DNS performance (there real slow). I have did a reverse dns via dnsstuff.com to make sure the IP is the correct ip for the domain and it was.

Here is another type of event I get:

Message delivery to the host '167.136.25.150' failed while delivering to the remote domain  'cargill.com' for the following reason: The remote server did not respond to a connection attempt.
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SembeeCommented:
Have you actually tried to manually connect to any of those domains.
You will need to an nslookup on the MX records and then telnet to the host listed on port 25.
http://www.amset.info/exchange/smtp-diag.asp

Where exactly did you enter the additional DNS Servers? In the DNS Server applet on the domain controllers or somewhere else?

Simon.

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dpickardAuthor Commented:
I entered it under System Manager > Administrative groups > First Administrative group > Servers > exchange02 > Protocols > Smtp and then whent to the properties of Default SMTP Virtual Server clicked the delivery tab and clicked advanced and clicked the configure button.
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SembeeCommented:
I would suggest that you remove them from there. That can cause problems.
The only place that DNS Severs should be entered is on the DNS Server applet. No where else.

Simon.

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dpickardAuthor Commented:
Below are the results from the dnsdiag which is a very nice tool. It would sometimes connect and other times it has the following. I had to create a yahoo id just so I could report the problem to yahoo. This happens even after changing the dns to only forward through the dns applet.


C:\SmtpDiag>smtpdiag "dpickard@plazare.com" "dpickard28@yahoo.com" /v

Searching for Exchange external DNS settings.
Computer name is EXCHANGE02.
VSI 1 has the following external DNS servers:
There are no external DNS servers configured.

Checking SOA for yahoo.com.
Checking external DNS servers.
Checking internal DNS servers.

Checking TCP/UDP SOA serial number using DNS server [192.168.18.15].
TCP test succeeded.
UDP test succeeded.
Serial number: 2007101813

Checking TCP/UDP SOA serial number using DNS server [192.168.18.10].
TCP test succeeded.
UDP test succeeded.
Serial number: 2007101813
SOA serial number match: Passed.

Checking local domain records.
Starting TCP and UDP DNS queries for the local domain. This test will try to
validate that DNS is set up correctly for inbound mail. This test can fail for
3 reasons.
    1) Local domain is not set up in DNS. Inbound mail cannot be routed to
local mailboxes.
    2) Firewall blocks TCP/UDP DNS queries. This will not affect inbound mail,
but will affect outbound mail.
    3) Internal DNS is unaware of external DNS settings. This is a valid
configuration for certain topologies.
Checking MX records using TCP: plazare.com.
  MX:    mx2.mailhop.org (20)
  MX:    mail.plazare.com (10)
  A:     mail.plazare.com [66.148.149.132]
Checking MX records using UDP: plazare.com.
  MX:    mail.plazare.com (10)
  MX:    mx2.mailhop.org (20)
  A:     mail.plazare.com [66.148.149.132]
Both TCP and UDP queries succeeded. Local DNS test passed.

Checking remote domain records.
Starting TCP and UDP DNS queries for the remote domain. This test will try to
validate that DNS is set up correctly for outbound mail. This test can fail for
3 reasons.
    1) Firewall blocks TCP/UDP queries which will block outbound mail. Windows
2000/NT Server requires TCP DNS queries. Windows Server 2003 will use UDP
queries first, then fall back to TCP queries.
    2) Internal DNS does not know how to query external domains. You must
either use an external DNS server or configure DNS server to query external
domains.
    3) Remote domain does not exist. Failure is expected.
Checking MX records using TCP: yahoo.com.
  MX:    d.mx.mail.yahoo.com (1)
  MX:    e.mx.mail.yahoo.com (1)
  MX:    f.mx.mail.yahoo.com (1)
  MX:    g.mx.mail.yahoo.com (1)
  MX:    a.mx.mail.yahoo.com (1)
  MX:    b.mx.mail.yahoo.com (1)
  MX:    c.mx.mail.yahoo.com (1)
  A:     d.mx.mail.yahoo.com [216.39.53.2]
  A:     e.mx.mail.yahoo.com [216.39.53.1]
  A:     f.mx.mail.yahoo.com [68.142.202.247]
  A:     f.mx.mail.yahoo.com [209.191.88.247]
  A:     g.mx.mail.yahoo.com [206.190.53.191]
  A:     g.mx.mail.yahoo.com [209.191.88.239]
  A:     a.mx.mail.yahoo.com [209.191.118.103]
  A:     b.mx.mail.yahoo.com [66.196.97.250]
  A:     c.mx.mail.yahoo.com [216.39.53.3]
  A:     c.mx.mail.yahoo.com [68.142.237.182]
Checking MX records using UDP: yahoo.com.
  MX:    e.mx.mail.yahoo.com (1)
  MX:    f.mx.mail.yahoo.com (1)
  MX:    g.mx.mail.yahoo.com (1)
  MX:    a.mx.mail.yahoo.com (1)
  MX:    b.mx.mail.yahoo.com (1)
  MX:    c.mx.mail.yahoo.com (1)
  MX:    d.mx.mail.yahoo.com (1)
Both TCP and UDP queries succeeded. Remote DNS test passed.

Checking MX servers listed for dpickard28@yahoo.com.
Connecting to c.mx.mail.yahoo.com [68.142.237.182] on port 25.
Received:
421 Message from (66.148.149.132) temporarily deferred - 4.16.50. Please refer t
o http://help.yahoo.com/help/us/mail/defer/defer-06.html


Error: Expected "220". Server is not accepting connections.
Failed to submit mail to c.mx.mail.yahoo.com.
Connecting to g.mx.mail.yahoo.com [209.191.88.239] on port 25.
Received:
421 Message from (66.148.149.132) temporarily deferred - 4.16.50. Please refer t
o http://help.yahoo.com/help/us/mail/defer/defer-06.html


Error: Expected "220". Server is not accepting connections.
Failed to submit mail to g.mx.mail.yahoo.com.
Connecting to f.mx.mail.yahoo.com [209.191.88.247] on port 25.
Received:
421 Message from (66.148.149.132) temporarily deferred - 4.16.50. Please refer t
o http://help.yahoo.com/help/us/mail/defer/defer-06.html


Error: Expected "220". Server is not accepting connections.
Failed to submit mail to f.mx.mail.yahoo.com.
Connecting to c.mx.mail.yahoo.com [216.39.53.3] on port 25.
Received:
220 mta325.mail.re4.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo plazare.com

Received:
250-mta325.mail.re4.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING


Sent:
mail from: <dpickard@plazare.com>

Received:
250 sender <dpickard@plazare.com> ok

Sent:
rcpt to: <dpickard28@yahoo.com>

Received:
250 recipient <dpickard28@yahoo.com> ok

Sent:
quit

Received:
221 mta325.mail.re4.yahoo.com

Successfully connected to c.mx.mail.yahoo.com.
Connecting to b.mx.mail.yahoo.com [66.196.97.250] on port 25.
Received:
421 Message from (66.148.149.132) temporarily deferred - 4.16.50. Please refer t
o http://help.yahoo.com/help/us/mail/defer/defer-06.html


Error: Expected "220". Server is not accepting connections.
Failed to submit mail to b.mx.mail.yahoo.com.
Connecting to a.mx.mail.yahoo.com [209.191.118.103] on port 25.
Received:
421 Message from (66.148.149.132) temporarily deferred - 4.16.50. Please refer t
o http://help.yahoo.com/help/us/mail/defer/defer-06.html


Error: Expected "220". Server is not accepting connections.
Failed to submit mail to a.mx.mail.yahoo.com.
Connecting to g.mx.mail.yahoo.com [206.190.53.191] on port 25.
Received:
421 Message from (66.148.149.132) temporarily deferred - 4.16.50. Please refer t
o http://help.yahoo.com/help/us/mail/defer/defer-06.html


Error: Expected "220". Server is not accepting connections.
Failed to submit mail to g.mx.mail.yahoo.com.
Connecting to f.mx.mail.yahoo.com [68.142.202.247] on port 25.
Received:
421 Message from (66.148.149.132) temporarily deferred - 4.16.50. Please refer t
o http://help.yahoo.com/help/us/mail/defer/defer-06.html


Error: Expected "220". Server is not accepting connections.
Failed to submit mail to f.mx.mail.yahoo.com.
Connecting to e.mx.mail.yahoo.com [216.39.53.1] on port 25.
Received:
421 Message from (66.148.149.132) temporarily deferred - 4.16.50. Please refer t
o http://help.yahoo.com/help/us/mail/defer/defer-06.html


Error: Expected "220". Server is not accepting connections.
Failed to submit mail to e.mx.mail.yahoo.com.
Connecting to d.mx.mail.yahoo.com [216.39.53.2] on port 25.
Received:
421 Message from (66.148.149.132) temporarily deferred - 4.16.50. Please refer t
o http://help.yahoo.com/help/us/mail/defer/defer-06.html


Error: Expected "220". Server is not accepting connections.
Failed to submit mail to d.mx.mail.yahoo.com.

C:\SmtpDiag>
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dpickardAuthor Commented:
I got with yahoo and it should be fixed now. I think I was on an internal greylist or something. I am assuming that the same thing is happening with verizon aswell. Thanks for the help.
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