Exchange 2003 outbound messages in queue for several days

Several messages to a couple of locations have been in queue for several days. The only thing I see is under additional queue information: An SMTP protocol error occurred

sergenetAsked:
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kieran_bCommented:
Are they legitimate mails?  If not, then it could simply be NDR spam, which will take a while to clear.  If the ARE legitimate mails, then I would be putting your domain and their domain into http://www.dnsreport.com and seeing what is happening.
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sergenetAuthor Commented:
They are legitimate emails. We have used them before. DNS lookup shows ok.
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kieran_bCommented:
Then it could be a problem between your server and them, the best test would be as follows;

Drop their domain into here -> http://www.zmailer.org/mxverify.html

Now, from the server itself, mimic the behaviour of that page.

Start > run > telnet server.domain.com 25 (the servername will be given to you by the page above)
ehlo yourdomain.com
mail from:you@yourdomain.com
rcpt to:someone@theirdomain.com
data
Subject: This is a test
Please reply
.

Let us know what error you get, if anything.

Did your domain throw any errors in DNS report?
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sergenetAuthor Commented:
It is coming up with no such domain for them. They must be down or have other problems.
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kieran_bCommented:
Try another domain that is queued then - if they all have problems, it aint you.
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sergenetAuthor Commented:
I was mistaken on the first one. I misspelled the name. It comes up ok and so do the others.
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kieran_bCommented:
Right, so have you tried the telnet test to send mail to them then?
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sergenetAuthor Commented:
I tried the test  telnet but I cannot go past the rcpt to:  no matter what email address I use, I get the following: 530 SMTP authentication is required.
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kieran_bCommented:
That is a recipient problem, they are requiring authentication - unless you know the password (which it is not reasonable for you to know) they are misconfigured.
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sergenetAuthor Commented:
When I look for additional queue information in system manager, all the queued emails have an SMTP protocol error has occurred. There are 3 domains that I am having problems with. They were working fine a few days ago and have been for a long time.  Any suggestions on what to do on my end?
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kieran_bCommented:
Put the three domains into http://www.zmailer.org/mxverify.html and see if it has an error - if it does, then it is their problem.  If it doesn't then it is your problem, and we will do more testing.
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sergenetAuthor Commented:
I tried 4 domains that are in the queue and they all come up ok.
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kieran_bCommented:
Even the one that was showing "authentication required"?

Anyway, if that is the case, try a telnet test from your server to these 4 domains individually -> http://www.amset.info/exchange/telnet-test.asp

Kieran
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sergenetAuthor Commented:
A colleague suggested I change the external ip address of the router which I did. Walla! The queue is empty. I changed the ip back to the old one and tried a new email to the same receipient, same thing, stuck in queue. Changed it again to the new ip and it went through. What is wrong? Is the ip blocked somehow? It does not show up on any black list.
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kieran_bCommented:
what is the ip?
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sergenetAuthor Commented:
64.60.132.131  This is the one that has the problem.
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kieran_bCommented:
That has a bad reverse DNS entry, what is the working one?
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sergenetAuthor Commented:
64.60.132.133
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sergenetAuthor Commented:
I still do not know what happened to the original IP address. If someone would like to pursue the matter, please let me know before I close the case. Thanks.
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kieran_bCommented:
I don't know.  Neither the original IP, nor the new IP has a good rdns entry.  Neither are on blacklists - and I can't connect to either of them...
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sergenetAuthor Commented:
What do you recommend I do? Shall I contact the dns hosting company and ask why we do not have a rdns entry? I do not want this to happen again in the future. If there is something that can be done from my end please let me know. Thanks kieran b.
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kieran_bCommented:
You would ask your ISP for an rDNS entry.

That the problem has mysteriously disappeared is the concerning part - I don't know what the cause was...
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