Issue with Sending and receiving email on Exchange 2003

Hi Experts,

Having some issues with my Exchange Server 2003 which is installed in a SBS2003 environment.
Have an untangle gateway in between.

At present cannot send or receive external emails... internal works fine.

Error number on returned emails is 4.4.7

Things tried so far -


Reboot stopped services restarted, checked error logs nothing conclusive.
Have used Exchange analyser and corrected a critical error relating to memory size, couple of non-critical errors.

MXtoolbox test - SMTP times out

Tried telnet test as per
http://www.amset.info/exchange/telnet-test.asp
Makes it to the end and then says "Message in que for delivery"

Mail just sits in the Exchange Server que until it eventually gives up.

Things that have changed for possible causes
  - My Server froze and I had to hard reboot... also not sure if related maybe just bad timing, some software upgrades took place that eveing at our local exchange not sure if this could have anything to do with Reverse lookup.

Firewall on Netgear router allows for port 25 incoming and outgoing with Windows firewall turned off.

Run out of ideas assuming it is SMTP or DNS issue can use internet fine (Still a novice on exchange)  HELP required please !!!

thanks.
AndrewPartnerAsked:
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AndrewConnect With a Mentor PartnerAuthor Commented:
Called the ISP it turned out the recent upgrade by the major telco had blocked port 25, thanks for your assistance much apprieciated.
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yelbaglfCommented:
Taken from the following KB:

http://support.microsoft.com/kb/284204

Numeric Code: 4.4.7

Possible Cause: The message in the queue has expired. The sending server tried to relay or deliver the message, but the action was not completed before the message expiration time occurred. This NDR may also indicate that a message header limit has been reached on a remote server or that some other protocol timeout occurred during communication with the remote server.

Troubleshooting: This code typically indicates an issue on the receiving server. Verify the validity of the recipient address, and verify that the receiving server is configured to receive messages correctly. You may have to reduce the number of recipients in the header of the message for the host that you are receiving this NDR from. If you resend the message, it is placed in the queue again. If the receiving server is on line, the message is delivered.

Also, are you sending emails with all caps, blank subject lines, or anything that might be caught as spam?  
Are there attachments involved?  
I'm guessing that the send/receive tests to/from external domains have been performed on more than one client machine?  
And also, have you tested to multiple external domains like gmail, hotmail, etc?  Are you blacklisted?
You can also check to insure you're not blacklisted and verify reverse DNS here:
http://www.mxtoolbox.com/

Double-check your MX records with your ISP.  Are you using a connector to relay outbound email through your ISP?
http://www.amset.info/exchange/smtp-connector.asp

Some receiving domains require the sending domain to have an SPF record.  This gets defined with your ISP, or whomever provides your public mail IP.
http://en.wikipedia.org/wiki/Sender_Policy_Framework

Microsoft even has a wizard to help guide you with creating an SPF record.
http://www.microsoft.com/mscorp/safety/content/technologies/senderid/wizard/
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AndrewPartnerAuthor Commented:
Hi Yelbaglf,

Thanks for your response

Has to my issue due to no mail in or out.

To answer your questions -
Also, are you sending emails with all caps, blank subject lines, or anything that might be caught as spam?  No
Are there attachments involved?  No
I'm guessing that the send/receive tests to/from external domains have been performed on more than one client machine?  Yes

Not blacklisted checked yesterday and again today.

Dont have a SPF record so will look at the SPF link (thanks for that) have tested a few domains but nothing coming in or going out.

Are you suggesting setting up a connector using the ISP would this get me around the issue for now?

MX records are held with Zoneedit

thanks.
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Radhakrishnan RSenior Technical LeadCommented:
Its looks like RDNS entry is not available for external, For that you have to contact your ISP for creating a PTR record for you exchange, You have to provide your public IP of the exchange server.

Hope this helps.
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AndrewPartnerAuthor Commented:
Thanks radhakrishnan2007

Will speak with the ISP about that... any reason why it would work for 18months and then just stop?
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yelbaglfCommented:
Just wanted to note something from my previous post...

You can also check to insure you're not blacklisted and verify reverse DNS here:
http://www.mxtoolbox.com/

From there you can verify your reverse DNS.  I also suggested contacting your ISP for verification, as well.
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yelbaglfCommented:
In reference to the smarthost...

What this does is help to minimize your chances of being blacklisted.  It's something that helps reduce spam.  If you were blacklisted, or if being blacklisted were an issue, then setting up the connector would alleviate.  In general, it's not a bad idea to do this anyways.

Another example would be using a smarthost with a spam filter solution like Postini or MXRecords.  Then your smarthost would be Postini or MXRecords respectively, instead of your ISP or none at all.  

http://en.wikipedia.org/wiki/Smart_host
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AndrewPartnerAuthor Commented:
thanks yelbaglf,

Nice points will look into your suggestions, I was blacklisted late last year due to fixing a clients badly infected PC which was a nightmare to sort, out so will definetly be looking into... thanks.
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AndrewPartnerAuthor Commented:
just ran Reverse lookup and that points to my ISP...
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yelbaglfCommented:
So when you run ptr:xxx.xxx.xxx.xxx, it should return your mail server's external IP address mapped to your mail server or OWA.
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yelbaglfConnect With a Mentor Commented:
Check with Zoneedit to insure that your rDNS is setup and working properly.  You should have a public IP for exchange through your ISP, and that IP should point to your mail server. (http://mail.server.com)
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yelbaglfCommented:
You are most welcome!  Gotta love upgrades! :-)
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AndrewPartnerAuthor Commented:
Sorry Yelbaglf... didnt realise the points didnt register wanted to give you some for helping out cheers.
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yelbaglfCommented:
Thanks for the points!  :-)
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