E-mail gets stuck in the queue with exchange 2003

About 25 percent of email gets stuck in the SMTP queue with exchange 2003.  It has been fine for years and just started.  When you look at the queue there is a message the an SMTP protocol error occurred.  After many hours the message gets sent back to the user saying that it was undeliverable and took too long to deliver.
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captjcretConnect With a Mentor Author Commented:
When I changed the DNS I was unable to send to anybody.  Changed it back to what it was and suddenly the whole thing is working fine!????? Nothing is sticking in the queue anymore.  I don't get it.
Alan HardistyCo-OwnerCommented:
This is usually down to incorrect configuration at your end or being blacklisted.

Please check your IP address on http://www.mxtoolbox.com/blacklists.aspx

Also - your FQDN configured on your server on the SMTP Virtual Server has to resolve in External DNS back to the IP Address you are sending from and you also need to make sure Reverse DNS is configured on your Fixed IP Address with an FQDN that also resolves back to the same IP Address.
What error code is that CaptJCRET
is it 5.5.7 / 5.5.1 ?

Please elucidate.

I'd go with Alan's suggestion first and eliminate those options.
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captjcretAuthor Commented:
From: System Administrator

Sent: Sunday, November 21, 2010 8:34 AM

To: Tina Schoneman

Subject: Undeliverable:Job Openings

Your message did not reach some or all of the intended recipients.

Subject: Job Openings

Sent: 11/19/2010 8:25 AM

The following recipient(s) could not be reached:

user@remotedomain.com on 11/21/2010 8:34 AM

Could not deliver the message in the time limit specified. Please retry or contact your administrator.

<SERVER.domain.local #4.4.7>

captjcretAuthor Commented:
They are not blacklisted
Alan HardistyConnect With a Mentor Co-OwnerCommented:
If your FQDN is SERVER.domain.local - then it is not configured correctly.  You need to be able to resolve the FQDN in DNS and .local domain names are internal only domains and CANNOT be resolved.

Please change your FQDN to something like mail.domain.com or whatever your domain name ends with.

It can be change on the SMTP Virtual Server (Properties)> Delivery Tab> Advanced Button.
It sounds to me that your ISP may have made a configuration change on their side.  I've seen this happen with Centurylink and Brighthouse quite a bit.

What happens is the RDNS is failing from what were previously accepted domains and the mail will sit in the queue until the retry timeout expires.

A call to your ISP might confirm this.  Sometimes it's as easy as a (R)DNS record change (sometimes you have to create a smart host on your ISP's network).

Hope this helps.

captjcretAuthor Commented:
I changed to full qualified domain name from what it was to mail.domain.com where I used thier domain name instead. When I clicked on check DNS it tells me it is not a valid domain
Alan HardistyConnect With a Mentor Co-OwnerCommented:
Do you have a record in DNS for your domain called mail.domain.com - bear in mind that I am only using mail.domain.com as an example - if your domain is Microsoft.com then it should read mail.microsoft.com

Whatever you use - has to resolve in DNS externally otherwise DNS lookup will fail.

If your domain ends .com - you don't have any A records setup - so mail.yourdomain.com will fail until you setup a new A record.  You don't have to use mail - you can use remote / bananas / poodles / Spock - the name is up to you - but you need to make sure you have a corresponding A record.
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.

a) go to mxtoolbox.com
enter the domain name of the *receiving server*
note down the first MX record listed.

lets say it is mail.domain.com

start > run > cmd
telnet mail.domain.com 25

See if you can get a SMTP 220 header.
If not - call the company and check if they are having any email issues.

captjcretAuthor Commented:
I am getting the SMTP  220 header.  I am noticing that the sites I am having problems with all have something to do with roadrunner.
Alan HardistyCo-OwnerCommented:
Any feedback to my last comment?
captjcretAuthor Commented:
Thanks for all your suggestions
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