Delivery has failed to these recipients or distribution lists:

We just upgraded our Exchange from 2003 to 2007 and everthing has been working fine some users are getting these messages on their inbox.  Not sure what the issue is.  I know we just updated our Ssl cert (not sure if that matters),.  
From: Microsoft Exchange
Sent: Thursday, December 10, 2009 3:21 PM
To: Milko
Subject: Undeliverable: I sent the Quote...

Delivery has failed to these recipients or distribution lists:

'adam@emaildomain.com' <mailto:adam@emaildomain.com> 
Microsoft Exchange has been trying to deliver this message without success and has stopped trying. Please try sending this message again, or provide the following diagnostic text to your system administrator.

  _____  

Sent by Microsoft Exchange Server 2007






Diagnostic information for administrators:

Generating server: msgsvr.domain.local

adam@emaildomain.com
#550 4.4.7 QUEUE.Expired; message expired ##

Original message headers:

Received: from msgsvr.domain.local ([192.168.1.6]) by msgsvr.domain.local
 ([192.168.1.6]) with mapi; Tue, 8 Dec 2009 15:19:18 -0800
From: Milko  <Milko@myemaildomain.com>
To: "'adam@emaildomain.com'" <adam@emaildomain.com>
Date: Tue, 8 Dec 2009 15:19:17 -0800
Subject: I sent the Quote...
Thread-Topic: I sent the Quote...
Thread-Index: Acp4XNqYeRlA1ckITbG6KB/yKlUOcQ==
Message-ID: <87EDF2574C700C4BA0B197FDA20E0DFF0F856874C2@msgsvr.domain.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
acceptlanguage: en-US
Content-Type: multipart/alternative;
        boundary="_000_87EDF2574C700C4BA0B197FDA20E0DFF0F856874C2msgsvrDomain_"
MIME-Version: 1.0

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kabrutusAsked:
Who is Participating?
 
Glen KnightConnect With a Mentor Commented:
Is it only happening to 1 domain?

Can you telnet to their server on port 25?
Goto http://www.mxtoolbox.com and enter the domain you ate trying to contact.

Make a note of the MX record.

Then from your exchange server do the following:
telnet mxrecord 25
replace mxrecord with the data you got from MXToolbox.

Then run through this document using your domain in the eulogy command, your email address as the mail from and the recipient you ate trying to reach as the rcpt to.

http://support.microsoft.com/kb/153119
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Glen KnightCommented:
These messages could have just been sat in the queues during the transition between exchange 2003 and 2007 and presumably you changed the rules for access in and out if your network from the Exchange 2003 server so it could no longer deliver mail.

It was probably just a handfull of messages and you will probably find it won't happen again.
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kabrutusAuthor Commented:
these are new emails sent out a few days ago.  We swapped out the server over 2 months ago.
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Glen KnightCommented:
Interesting.
This could also be caused by spam/virus software on the exchange server?

What software do you have insalled?
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MesthaCommented:
The error is a straight time out.
The most common reasons for that are all out of your control. If you look in the queue viewer you should be able to see if there are any other messages in the queues.

Shouldn't have anything to do with SSL certificate changes - at most that would cause a problem with inbound email, not outbound.

Simon.
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kabrutusAuthor Commented:
all I have symantec end point protection 11 and our spam is hosted by mcafee.  

I thought so too. But we are getting a lot of these delays and fails from our client emails.  We never had this with exchane 2003.
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MesthaCommented:
When it comes to email delivery, what happened in the past doesn't matter a jot. Email delivery is a moving target - things can work now and in ten minutes time fail and most of the time it is out of your control.

What is between the server and the Internet? Firewall of some kind? Does it do SMTP scanning?
You referred to McAfee - is that their hosted solution? If so, do you route email out through their service as well? If not, do you deliver email directly or via another smart host?

If direct - are your DNS and PTR records configured correctly? The correct SMTP FQDN set on the Send Connector?

Simon.
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memo_tntCommented:
hi
such issues caused from wrong a cache entry on the local outlook .NK2

so, be sure of the recipient you are trying to send to,, try to add it manually
and dont get any cached entry,,

if didnt solve that then follow these steps one by one and not at the same time:

1- Delete the Outlook clients nickname cache file by searching the local Outlook profile for a .NK2 file and deleting it.  
2- Change the Outlook to non-cached mode to ensure it is not a cached entry from the Offline Address Book.  
3- Check the behaviour in OWA to confirm the server is generating the correct address list and has updated the GAL.


best regards


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peakpeakCommented:
First of all, are these internal emails only (it is according to your example). Has the sender actually sent this email to the recipient?
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kabrutusAuthor Commented:
I have been sending emails to these same clients for years.  My email server is behind a sonicwall firewall without smtp scanning.  We have Mcafee hosted service but this is only a spam filter and only handles inbound not outbound.  I am currently looking into the PTR/DNS to see if they are configured correctly.
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peakpeakCommented:
Ok, but you didn't answer my question ....
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kabrutusAuthor Commented:
yes.  We have sent this client emails before and received.  This is one of our major clients.
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peakpeakCommented:
Yet no answer: Internal only? (according to your example)
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kabrutusAuthor Commented:
Sorry i meant to say they are external emails.  they are not part of our exchange server.
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kabrutusAuthor Commented:
My user (exchange) sent an email to our client Adam(not-exchange), My user(exchange) got this "Delivery has failed to these recipients or distribution lists" in his inbox.  

Not sure i am explaining it right...
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peakpeakCommented:
Please answer this:
a) How many users are affected by this?
b) How many recipients are contained in the bounce? (i.e local employees)
c) How many non-reachable recipients are there? (i.e. external)
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peakpeakCommented:
My guess it's one only, am I correct?
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kabrutusAuthor Commented:
Its kind of slow for us right now with the holidays, but i would say
a) From what i know its about 4 users
b) 1
c) 5 so far

most of the users are out but will be returning in Jan.  I cant get an actual account yet.  I just want to fix the problem before it becomes a huge issue.
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peakpeakCommented:
Ok, easy, send the recipient an email from an external account, like hotmail ... do you get a bounce?
If Yes, the problem lies on the receiving side (not you)
if No you need to investigate further: spam handling, black lists and also try this:
Send from an employee who has never mailed this person before ... tell me success or failure along with the (possible) error message (bounce)
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peakpeakCommented:
Forgot the obvious issue: Is there someone who actually succeed in mailing this person?
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MesthaCommented:
It should now be obvious that when it comes to email, previous behaviour is not an indication that things will continue to work correctly or that your system was setup in the right way.
The fight against spam is a war and things change very quickly. Something can work now, and in 24 hours time it will stop working.

The original error is a timeout error - meaning that your server was unable to connect to the remote server for some reason.

Simon.
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kabrutusAuthor Commented:
When i telneted into their server i got the following.  please see attached.  Does that mean there is a problem with my servers configuration?
Screen-shot-2009-12-29-at-4.14.2.png
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peakpeakCommented:
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Glen KnightCommented:
Have a read through this FAQ from ESe member alanhardisty: http://www.it-eye.co.uk/faqs/readQuestion.php?qid=2
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kabrutusAuthor Commented:
I ran through the anti abuse.org website and my ip came up as not blacklisted.  I dont understand why that email server would reject me if i am not blacklisted.
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Glen KnightCommented:
Did you go through the FAQ i posted?
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MesthaConnect With a Mentor Commented:
SecureSever.net is GoDaddy's email system and is one of the biggest email clusters in the world. They will almost certainly be operating their own blacklists.

Simon.
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kabrutusAuthor Commented:
I think you are correct about SecureServer.net.  I just did an mx lookup on other domains we are having issues on and they are all part of this SecureServer.net.  I sent a request to unblock us yesterday and i telneted in to the server that denied me yesterday and i was able to get this(see attached)

Can i assume the issue is with godaddy blacklisting us?
Screen-shot-2009-12-30-at-11.15..png
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kabrutusAuthor Commented:
I am currently having our users email their clients to see if they receive emails from us.
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Glen KnightCommented:
Yes and if you can now get access then you have been removed from the blacklist.
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kabrutusAuthor Commented:
We were black listed with godaddy only.  Once we sent the unblock request we were able send E-mails to all domains.
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