This server requires PTR for unauthenticated connections

Hi,
I'm having this PTR problem when sending to this one particular domain. The the problem happens very intermittently. Sometimes the email would send through but other times it bounces back "The following recipient(s) could not be reached:

      geoff@robinskitchen.com.au on 3/07/2009 8:41 AM
            There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
            <mail.meyerau.com.au #5.5.0 smtp;554 This server requires PTR for unauthenticated connections.>"
I'm running exchange 2003 internally but our MX records are pointed to messagelabs to do spam filtering (please see attachment for my dns setting). I'm able to send/receive emails from everyone else but this particular domain. What should i do to resolve this problem?  
 
forward-dns.jpg
hvleInformation Systems ManagerAsked:
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kevin_uCommented:
The problem is not your MX nor anything to do with your incoming mail server.

It has to do with your outgoing server.  If you're using Exchange to deliver mail directly (as opposed to forwarding every email to your ISP), then your public IP must have a reverse dns entry (PTR record).   The mail server you are sending to may additionally require that your forward record match (your IP's main host name).

You need to deal with your ISP on this because they are in control over your reverse dns entries.  You may have a tool that your ISP provided as well that lets you set the reverse host name.

An alternative is to set up all outgoing emails to go through your ISP's mail server.  (called smart host or forwarding)

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KaffiendCommented:
A PTR record exists in a Reverse DNS zone, not in a Forward DNS zone.  The pic above doesn't say much about whether your organization's mail server has a PTR record or not.  
Go to this site:  http://ping.eu
Plug in your mail server's public IP address, and see if there is a valid, non-generic Reverse DNS record or not

Have your ISP create a PTR record for the (public) IP address that your email server uses when it sends mail.  

(If you send outgoing mail through a smart host, then yell at the smart host provider, and have them create a PTR record for their server)
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tmeunierCommented:
Yes, this DNS zone is sort of messed up.  You have mail.meyerau.com.au CNAMEd over to MX8.whatever.messagelabs.  That isn't correct, unless mail.meyerau.com.au is actually the exact identical public IP address, exact identical server, as MX8.whatever.messagelabs.   Since Message Labs is capable of sending your mail to you, I know that mail.meyerau.com.au has a fixed public IP address. Use this as an "A" record, and remove the CNAME.  Then, let's say that this IP address is 210.11.113.90.  You need to go to your ISP (unless you've been delegated reverse DNS) and tell them you need them to create the PTR record as follows:
90.113.11.210.in-addr.arpa   IN    PTR    mail.meyerau.com.au.

There is no reason I can see to have your actual mail host CNAMEd to Message Labs' MX.

-tom
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hvleInformation Systems ManagerAuthor Commented:
I have asked my ISP to add the PTR record. it looks like it's working. thank you
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hvleInformation Systems ManagerAuthor Commented:
Hi,
I have asked my ISP to add the PTR record for 165.228.149.138 to point to mail.meyerau.com.au and i have used  http://ping.eu to check and it's valid. I've waited for 1 week for all the DNS in the world to replicate across but the email still bounce back with the same error message "Your message did not reach some or all of the intended recipients.

      Subject:      test
      Sent:      6/08/2009 4:14 PM

The following recipient(s) cannot be reached:

      sales@robinskitchen.com.au on 6/08/2009 4:14 PM
            There was a SMTP communication problem with the recipient's email server.  Please contact your system administrator.
            <mail.meyerau.com.au #5.5.0 smtp;554 This server requires PTR for unauthenticated connections.>"

Have I missed something? or did I do anything incorrectly?  

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KaffiendCommented:
Well, it certainly looks like you've done everything right.

Your DNS A Record, and PTR record look good.
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tmeunierCommented:
Indeed they look good.  You may need to wait 24 hours from the time the PTR was created, if that mail host (robinskitchen.com.au) had cached whatever placeholder the ISP had there before.
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