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Problem with mail delivery from Small Business Server 2003 (exchange 2003)

I have a user who is getting mail rejected and I want to try and determine which server the message is referring to. i.e. the destination or originator (Exchange)

This server is configured with the SBS Internet connection Wizard and mail is being delivered using DNS. There is a PTR record setup for the IP address of the mail server at the ISP.

It's generally working OK but the user has had a couple of messages rejected. I'm not sure if this may be due to blacklisting.

When I telnet to the originating server on port 25 the message returned looks OK.

The bounce message is as follows.

Your message did not reach some or all of the intended recipients.
      Subject:  RE: xxxxxxx
      Sent:     04/10/2007 09:48
The following recipient(s) cannot be reached:
      John Doe on 04/10/2007 09:48
            The message cannot be delivered due to a configuration error on the server. Please contact your Administrator.
            <mail.domain.com #5.3.0 smtp;553 5.3.0 smtp rejected from 111.222.333.444>
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Milkybar-kid
Asked:
Milkybar-kid
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1 Solution
 
SembeeCommented:
Is the IP address in the NDR yours?
In cases like this what tends to happen is the remote server rejects the message at the point of delivery, forcing the sending server to generate the NDR, which is then shown in the message.

Simon.
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Milkybar-kidAuthor Commented:
Yes the IP is the originating server. Where is the configuration error? at the originating server or the receiving server ?
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SembeeCommented:
If the IP address is the originating server then the problem is most likely to be with that machine. However it could be an issue with the remote server in that they are rejecting your message based on old information, a misconfiguration or something else.

Have you checked for blacklisting?
Have you checked your DNS, reverse DNS and server banner is correct? dnsreport.com will help with that. Look in the mail server section for errors.

Simon.
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Milkybar-kidAuthor Commented:
DNS is correct, PTR is correct. Mail Banner is correct. Have checked blacklists at mxtoolbox.com and it shows up the fiveten lists but that is down to the IP range at Eclipse Internet.

It's odd because mail from this domain and all other systems I have connected to Eclipse Internet cannot send mail to BT Internet / Openworld email addresses. Mail isn't rejected it just gets lost. It doesn't even get put into the spam folder at the BT address.
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SembeeCommented:
Does the email actually get delivered to BT's servers? Message tracking will show that.

Simon.
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Milkybar-kidAuthor Commented:
Message tracking in Exchange ? - Can you refer me to any documentation to set that up please ?
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SembeeCommented:
I have a brief guide here: http://www.amset.info/exchange/message-tracking.asp

You have to enable it and then wait for the problem.

Simon.
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Milkybar-kidAuthor Commented:
I enabled logging sent a message to BT and received :-
"Message transferred to mta834.mail.ukl.yahoo.com through SMTP"
So far nothing has arrived. Am I likely to see any tracking information come back or is it just lost in the BT (Yahoo) network now ?
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SembeeCommented:
If that is what Message tracking shows, then the message has been delivered to their servers. It is either lost of has been silently dropped. It could also be in the junk mail folder.

Simon.

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If your question has been answered, pleased remember to accept the answer and close the question.
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Milkybar-kidAuthor Commented:
Hmm. It's certainly not going to Junk.
Do ISP's actually just trash mail without a NDR ?
I guess there's no point trying to ask BT where it's going. I've contacted Eclipse but not holding my breath for them either :(
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SembeeCommented:
Eclipse will have nothing to do with it unless you were sending email through their servers. I use Eclipse myself and have them on a number of sites and haven't had any problems. BT on the other hand....

ISPs will drop email without an NDR. If they are confident it is spam or looks like spam then they will drop it.

Simon.

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If your question has been answered, pleased remember to accept the answer and close the question.
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Milkybar-kidAuthor Commented:
It's curious because as well as my customers I too am connected via Eclipse. I also have an account with BT Yahoo that I use for testing. I have a number of servers connected via Eclipse and all of them cannot deliver mail to BT Internet. Other servers with identical configurations are at another ISP (Enta) are able to send to BT no problem. You're right Eclipse don't want to know yet the problems seems to exist whether the mail is sent via dns or via smtp.eclipse.co.uk. I also pointed out to them that even if sending via dns their IP range is in the equation via the PTR record. How is your email configured ? I assume you run your email on exchange ? Can you send mail to BT Internet - it would be interesting to get you to send a message to my BT Internet account - is that possible ? I don't really want to post the address on here.
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SembeeCommented:
I have as little to do with BT as I can, they provide my phone line and that is all. I don't actually correspond with anyone regularly on BT Internet accounts, so it has never been an issue for me. I do have a few domains that I cannot send email to, so I bounce those messages off another server.

As far as the ISP is concerned the message is being delivered. The message tracking logs show that. What happens with the message is out of your hands.

I compare email delivery to the post. You can usually get a proof of delivery to the front door. However you do not know if the receptionist signs for the item and then simply drops in to a shredder. It is only when your correspondent asks where the item is that you know it hasn't arrived.
The "receptionist" will tell you that the item was dropped, if you are lucky, but not why the item was considered junk.  

You could try sending an email manually via telnet to see if that gets delivered, you could try forcing Outlook to use plain text and/or bouncing email off another server.

Unfortunately ISPs are law to themselves and when you are stuck like this, there is very little that you can do.

There is no point sending me your email address as I don't use my Exchange account for EE work and keep ee work out of my Exchange system. That is for client communication only.

Simon.

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If your question has been answered, pleased remember to accept the answer and close the question.
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Milkybar-kidAuthor Commented:
OK Simon - I understand.

Thank you.
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