Problem sending Messages to some domains

I am having difficulty sending messages to some domains.  Others work fine.  Using Windows 2008 R2 running Exchange Server 2013 Enterprise. We get a few "delayed" messages then a final unable to deliver message (in the following message - only one of the recipients did not receive the message:

Diagnostic information for administrators:

Generating server: FW-DC-1.Falcor.local


laurie@media-rich.com
Remote Server returned '550 4.4.7 QUEUE.Expired; message expired'


Original message headers:

Received: from FW-DC-1.Falcor.local (192.168.14.5) by FW-DC-1.Falcor.local
 (192.168.14.5) with Microsoft SMTP Server (TLS) id 15.0.620.29; Sat, 29 Mar
 2014 07:31:56 -0700
Received: from FW-DC-1.Falcor.local ([fe80::f9eb:a030:4068:634]) by
 FW-DC-1.Falcor.local ([fe80::f9eb:a030:4068:634%11]) with mapi id
 15.00.0620.020; Sat, 29 Mar 2014 07:31:56 -0700
From: Laurie Rich <Laurie@FalcorWines.com>
To: "Lance Stafford (lance@jensensornamental.com)"
      <lance@jensensornamental.com>
CC: "Jim Peterson (JCPeterson@hpcbd.com)" <JCPeterson@hpcbd.com>,
      "'laurie@media-rich.com'" <laurie@media-rich.com>
Subject: door drawings
Thread-Topic: door drawings
Thread-Index: Ac9LW+J8Y+0N4FYXTUqOm0CZeZTh0A==
Importance: high
X-Priority: 1
Date: Sat, 29 Mar 2014 14:31:56 +0000
Message-ID: <4af3f1ec0ea346c88773212a7fd328df@FW-DC-1.Falcor.local>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator:
x-vipre-scanned: 58717D69006CB058717EB6
x-originating-ip: [50.131.168.70]
x-gfi-smtp-submission: 1
x-gfi-smtp-hellodomain: FW-DC-1.Falcor.local
x-gfi-smtp-remoteip: 192.168.14.5
Content-Type: multipart/mixed;
      boundary="_005_4af3f1ec0ea346c88773212a7fd328dfFWDC1Falcorlocal_"
MIME-Version: 1.0


I have verified that the domain or IP address is not on any blacklist that I can find.  I used mxtoolbox.

No idea where to go on this.
HCPCJJ1Asked:
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HCPCJJ1Connect With a Mentor Author Commented:
Problem turned out to be a DNS issue.  The server would successfully resolve some hostnames and not others.  Had never seen that before.  All of the DNS settings appeared to be correct on the server.  Reboot of the server fixed the issue.
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Simon Butler (Sembee)ConsultantCommented:
The NDR doesn't really help in this instance. The message delivery failed because it was in the queue too long.

You need to look in the queue viewer to see whether anything is being returned - that will show you more than the NDR.

From the server itself, I would also attempt a telnet test to port 25 of the remote MX record host and see if you can connect.

Simon.
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HCPCJJ1Author Commented:
It is multiple domains that I cannot send to.   Nonetheless I tried TELNET to one of them.  I am able to connect,  and everything was well until the RCPT TO and I get an error:

502 unimplemented (#5.5.1)

Here is the message queue on one of the delayed messages:

Identity: FW-DC-1\89161\31881542238271
Subject: Test #1
Internet Message ID: <10b05b74e830439d87dd693ea48193c2@FW-DC-1.Falcor.local>
From Address: Laurie@FalcorWines.com
Status: Ready
Size (KB): 4
Message Source Name: SMTP:Default FW-DC-1
Source IP: 192.168.14.5
SCL: -1
Date Received: 3/31/2014 5:49:39 AM
Expiration Time: 4/2/2014 5:49:39 AM
Last Error:
Queue ID: FW-DC-1\89161
Recipients:  laurie@media-rich.com;2;2;[{LRT=};{LED=};{FQDN=};{IP=}];0;CN=Internet,CN=Connections,CN=Exchange Routing Group (DWBGZMFD01QNBJR),CN=Routing Groups,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=Falcor,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=Falcor,DC=local
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Simon Butler (Sembee)ConsultantCommented:
Do an nslookup on the domains you have a problem with and see if there is any common host - for example they are on Office365. It isn't unusual for an issue like this to be affecting multiple domains if they are on the same service.

Simon.
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HCPCJJ1Author Commented:
I ran two different ones and didn't see a common host.  Let's simplify and narrow it down to one host that I cannot send to.  I have domain control over both hosts so it should make troubleshooting easier.

1.  I cannot send a message to XXXXX@media-rich.com from XXXXX@falcorwines.com.  I will get a couple of "delay" messages and then a final NDR with no specific reason listed in either.

2.  I CAN send to XXXXX@media-rich.com from some of my other accounts and it goes through immediately.

3.  XXXXX@media-rich.com IS hosted by Office365.

4.  Message from XXXXX@falcorwines.com is sent via Exchange 2013

5.  I can successfully send a message from XXXXX@falcorwines.com to some of my other domains.
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Simon Butler (Sembee)ConsultantCommented:
That is why I said you need to look in the queue viewer. That will tell you if there is a temporary NDR being returned (which wouldn't be on the final NDR).

Simon.
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HCPCJJ1Author Commented:
Here is what is in the queue viewer as it relates to the previous post:

Identity: FW-DC-1\89161\31881542238271
Subject: Test #1
Internet Message ID: <10b05b74e830439d87dd693ea48193c2@FW-DC-1.Falcor.local>
From Address: Laurie@FalcorWines.com
Status: Ready
Size (KB): 4
Message Source Name: SMTP:Default FW-DC-1
Source IP: 192.168.14.5
SCL: -1
Date Received: 3/31/2014 5:49:39 AM
Expiration Time: 4/2/2014 5:49:39 AM
Last Error:
Queue ID: FW-DC-1\89161
Recipients:  laurie@media-rich.com;2;2;[{LRT=};{LED=};{FQDN=};{IP=}];0;CN=Internet,CN=Connections,CN=Exchange Routing Group (DWBGZMFD01QNBJR),CN=Routing Groups,CN=Exchange Administrative Group (FYDIBOHF23SPDLT),CN=Administrative Groups,CN=Falcor,CN=Microsoft Exchange,CN=Services,CN=Configuration,DC=Falcor,DC=local
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Simon Butler (Sembee)ConsultantCommented:
There should be more than that - that is a ready queue. If the message is being delayed it would be in a retry queue.

Simon.
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HCPCJJ1Author Commented:
Successfully resolved DNS issue.
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