exchange 2010, outlook

the following user paul is getting below error.

as per attached jpeg file, there are too many hops, what does this mean and how should I correct this.
error.jpg
pramod1Asked:
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Scott CSenior EngineerCommented:
When you send an email message it goes through several computers before it gets to its final destination.  Each transfer is a hop.  

There is not much you can to do fix the issue.  You need to check out to see if there is a forwarding loop.  If you know it's not a forwarding loop, you can ask the system admin to increase the maximum number of hops allowed.

Distribution lists can sometimes make troubleshooting the issue difficult.

To figure out the problems addresses(s) you will need to send test emails to smaller groups or individual users to narrow down where the issue is coming from.
AmitIT ArchitectCommented:
First check, if you have duplicate smtp address for this user. You can run ldap query in AD to check it.

Also, check this article:
https://exchangeserverpro.com/exchange-2007-2010-infinite-loops-internal-relay-domains/
pramod1Author Commented:
how to run ldap query
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We’d all like to think our company’s data is well protected, but when you ask IT professionals they admit the data probably is not as safe as it could be.

pramod1Author Commented:
he has multiple email address but his primary email is @clearchannel.com
AmitIT ArchitectCommented:
Check the article I posted first.
pramod1Author Commented:
he mail box is on 0365
AmitIT ArchitectCommented:
Is this hybrid?
pramod1Author Commented:
yes
pramod1Author Commented:
we did hybrid configuration wizrd and moved his mail box

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pramod1Author Commented:
the target address is not blank in ADSIEDIT

it has @domain.com also mail.onmicrosoft.com
pramod1Author Commented:
I did email address diagnostics in proof point our company's gateway

I am attaching the document. at end it says queued for delivery?

can you make out anything
EMAIL-SEARCH.docx
pramod1Author Commented:
Delivery has failed to these recipients or groups:
paulkrakovsky@clearchannel.com


A problem occurred during the delivery of this message. Please try to resend the message later. If the problem continues, contact your helpdesk.





Diagnostic information for administrators:
Generating server: mx0b-001b1801.pphosted.com
paulkrakovsky@clearchannel.com
#< #5.4.6 SMTP; 554 5.4.6 Too many hops> #SMTP#
Original message headers:
Return-Path: <PramodKumar@iheartmedia.com>
Received: from pps.filterd (m0077987.ppops.net [127.0.0.1])      by
 mx0b-001b1801.pphosted.com (8.15.0.59/8.15.0.59) with SMTP id t9CG9kCk011922
      for <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 11:12:26 -0500
Received: from hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com
 [207.230.136.6])      by mx0b-001b1801.pphosted.com with ESMTP id 1xgaqjbg40-1
      (version=TLSv1/SSLv3 cipher=AES128-SHA bits=128 verify=OK)      for
 <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 11:12:25 -0500
Received: from mx0a-001b1801.pphosted.com (148.163.156.6) by
 hybridhubin.iheartmedia.com (10.121.10.52) with Microsoft SMTP Server (TLS)
 id 14.3.235.1; Mon, 12 Oct 2015 10:57:20 -0500
Received: from pps.filterd (m0077983.ppops.net [127.0.0.1])      by
 mx0a-001b1801.pphosted.com (8.15.0.59/8.15.0.59) with SMTP id t9CFrZM0027559
      for <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:57:20 -0500
Received: from hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com
 [207.230.136.5])      by mx0a-001b1801.pphosted.com with ESMTP id 1xevqg6j8e-3
      (version=TLSv1/SSLv3 cipher=AES128-SHA bits=128 verify=OK)      for
 <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:57:19 -0500
Received: from mx0b-001b1801.pphosted.com (148.163.158.1) by
 hybridhubin.iheartmedia.com (10.121.10.51) with Microsoft SMTP Server (TLS)
 id 14.3.235.1; Mon, 12 Oct 2015 10:42:15 -0500
Received: from pps.filterd (m0077986.ppops.net [127.0.0.1])      by
 mx0b-001b1801.pphosted.com (8.15.0.59/8.15.0.59) with SMTP id t9CFc9ZG022528
      for <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:42:15 -0500
Received: from hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com
 [207.230.136.1])      by mx0b-001b1801.pphosted.com with ESMTP id 1xeww7x5kc-5
      (version=TLSv1/SSLv3 cipher=AES128-SHA bits=128 verify=OK)      for
 <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:42:14 -0500
Received: from mx0a-001b1801.pphosted.com (148.163.156.6) by
 hybridhubin.iheartmedia.com (10.121.10.31) with Microsoft SMTP Server (TLS)
 id 14.3.235.1; Mon, 12 Oct 2015 10:27:05 -0500
Received: from pps.filterd (m0077984.ppops.net [127.0.0.1])      by
 mx0a-001b1801.pphosted.com (8.15.0.59/8.15.0.59) with SMTP id t9CFH8hg015710
      for <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:27:05 -0500
Received: from hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com
 [207.230.136.6])      by mx0a-001b1801.pphosted.com with ESMTP id 1xew68pc9n-2
      (version=TLSv1/SSLv3 cipher=AES128-SHA bits=128 verify=OK)      for
 <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:27:04 -0500
Received: from mx0a-001b1801.pphosted.com (148.163.156.6) by
 hybridhubin.iheartmedia.com (10.121.10.52) with Microsoft SMTP Server (TLS)
 id 14.3.235.1; Mon, 12 Oct 2015 10:26:31 -0500
Received: from pps.filterd (m0077984.ppops.net [127.0.0.1])      by
 mx0a-001b1801.pphosted.com (8.15.0.59/8.15.0.59) with SMTP id t9CFEafI013035
      for <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:26:30 -0500
Received: from hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com
 [207.230.136.5])      by mx0a-001b1801.pphosted.com with ESMTP id 1xew68pc51-4
      (version=TLSv1/SSLv3 cipher=AES128-SHA bits=128 verify=OK)      for
 <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:26:29 -0500
Received: from mx0b-001b1801.pphosted.com (148.163.158.1) by
 hybridhubin.iheartmedia.com (10.121.10.51) with Microsoft SMTP Server (TLS)
 id 14.3.235.1; Mon, 12 Oct 2015 10:25:50 -0500
Received: from pps.filterd (m0077987.ppops.net [127.0.0.1])      by
 mx0b-001b1801.pphosted.com (8.15.0.59/8.15.0.59) with SMTP id t9CFEaJN025718
      for <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:25:50 -0500
Received: from hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com
 [207.230.136.2])      by mx0b-001b1801.pphosted.com with ESMTP id 1xgaqjb01k-3
      (version=TLSv1/SSLv3 cipher=AES128-SHA bits=128 verify=OK)      for
 <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:25:49 -0500
Received: from mx0a-001b1801.pphosted.com (148.163.156.6) by
 hybridhubin.iheartmedia.com (10.121.10.32) with Microsoft SMTP Server (TLS)
 id 14.3.235.1; Mon, 12 Oct 2015 10:25:47 -0500
Received: from pps.filterd (m0077984.ppops.net [127.0.0.1])      by
 mx0a-001b1801.pphosted.com (8.15.0.59/8.15.0.59) with SMTP id t9CFH8hL015710
      for <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:25:47 -0500
Received: from hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com
 [207.230.136.4])      by mx0a-001b1801.pphosted.com with ESMTP id 1xew68pbx0-2
      (version=TLSv1/SSLv3 cipher=AES128-SHA bits=128 verify=OK)      for
 <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:25:46 -0500
Received: from mx0a-001b1801.pphosted.com (148.163.156.6) by
 hybridhubin.iheartmedia.com (10.121.10.34) with Microsoft SMTP Server (TLS)
 id 14.3.235.1; Mon, 12 Oct 2015 10:25:43 -0500
Received: from pps.filterd (m0077983.ppops.net [127.0.0.1])      by
 mx0a-001b1801.pphosted.com (8.15.0.59/8.15.0.59) with SMTP id t9CFEYL8022525
      for <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:25:43 -0500
Received: from hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com
 [207.230.136.2])      by mx0a-001b1801.pphosted.com with ESMTP id 1xevqg68x4-2
      (version=TLSv1/SSLv3 cipher=AES128-SHA bits=128 verify=OK)      for
 <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:25:42 -0500
Received: from mx0b-001b1801.pphosted.com (148.163.158.1) by
 hybridhubin.iheartmedia.com (10.121.10.32) with Microsoft SMTP Server (TLS)
 id 14.3.235.1; Mon, 12 Oct 2015 10:25:30 -0500
Received: from pps.filterd (m0077986.ppops.net [127.0.0.1])      by
 mx0b-001b1801.pphosted.com (8.15.0.59/8.15.0.59) with SMTP id t9CFElKw032198
      for <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:25:29 -0500
Received: from hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com
 [207.230.136.2])      by mx0b-001b1801.pphosted.com with ESMTP id 1xeww7wymb-1
      (version=TLSv1/SSLv3 cipher=AES128-SHA bits=128 verify=OK)      for
 <paulkrakovsky@clearchannel.com>; Mon, 12 Oct 2015 10:25:29 -0500
Received: from EX10MBX02.usa.ccu.clearchannel.com ([fe80::750c:82c:4337:66cd])
 by EX10HUB02.usa.ccu.clearchannel.com ([::1]) with mapi id 14.03.0235.001;
 Mon, 12 Oct 2015 10:25:27 -0500
Content-Type: multipart/mixed;
      boundary="_000_4F5CDB2D108EAD49B8628D875A156336C60D10EX10MBX02usaccucl_"
From: "Kumar, Pramod" <PramodKumar@iheartmedia.com>
To: "Sis, John" <jsis@iheartmedia.com>, "Krakovsky, Paul"
      <paulkrakovsky@clearchannel.com>
Subject: RE: Still having problems with email bounceback
Thread-Topic: Still having problems with email bounceback
Thread-Index: AdEBLWLOvQwfBS8HTu6zkIp93qxkkgAAFGSQAACYDpAAAM8RYAABUHQgAOuA1lAABuEq0A==
Date: Mon, 12 Oct 2015 15:25:27 +0000
Message-ID: <4F5CDB2D108EAD49B8628D875A156336C60D10@EX10MBX02.usa.ccu.clearchannel.com>
References: <CY1PR0601MB1628ACF58EEF5B08D4A8DE7BB1360@CY1PR0601MB1628.namprd06.prod.outlook.com>
 <DM2PR0601MB1311C3E42EE68B258507480BD1360@DM2PR0601MB1311.namprd06.prod.outlook.com>
 <DM2PR0601MB1295F05B0CE2403B092474E2B5360@DM2PR0601MB1295.namprd06.prod.outlook.com>
 <4F5CDB2D108EAD49B8628D875A156336C5C294@EX10MBX02.usa.ccu.clearchannel.com>
 <4F5CDB2D108EAD49B8628D875A156336C5C3DD@EX10MBX02.usa.ccu.clearchannel.com>
 <BN3PR0601MB130073965CB4253C51CCDC4ED1310@BN3PR0601MB1300.namprd06.prod.outlook.com>
In-Reply-To: <BN3PR0601MB130073965CB4253C51CCDC4ED1310@BN3PR0601MB1300.namprd06.prod.outlook.com>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator: <4F5CDB2D108EAD49B8628D875A156336C60D10@EX10MBX02.usa.ccu.clearchannel.com>
x-originating-ip: [10.121.2.3]
MIME-Version: 1.0
X-OrganizationHeadersPreserved: EX10HUB02.usa.ccu.clearchannel.com
X-Proofpoint-Virus-Version: vendor=fsecure engine=2.50.10432:,, definitions=2015-10-12_08:,,
 signatures=0
X-CrossPremisesHeadersFiltered: EX10HUB02.usa.ccu.clearchannel.com
X-OrganizationHeadersPreserved: EX10HUB02.usa.ccu.clearchannel.com
X-Proofpoint-Virus-Version: vendor=fsecure engine=2.50.10432:,, definitions=2015-10-12_08:,,
 signatures=0
X-CrossPremisesHeadersFiltered: EX10HUB04.usa.ccu.clearchannel.com
X-OrganizationHeadersPreserved: EX10HUB04.usa.ccu.clearchannel.com
X-Proofpoint-Virus-Version: vendor=fsecure engine=2.50.10432:,, definitions=2015-10-12_08:,,
 signatures=0
X-CrossPremisesHeadersFiltered: EX10HUB02.usa.ccu.clearchannel.com
X-OrganizationHeadersPreserved: EX10HUB02.usa.ccu.clearchannel.com
X-Proofpoint-Virus-Version: vendor=fsecure engine=2.50.10432:,, definitions=2015-10-12_08:,,
 signatures=0
X-CrossPremisesHeadersFiltered: EX10HYB01SAT.usa.ccu.clearchannel.com
X-OrganizationHeadersPreserved: EX10HYB01SAT.usa.ccu.clearchannel.com
X-Proofpoint-Virus-Version: vendor=fsecure engine=2.50.10432:,, definitions=2015-10-12_08:,,
 signatures=0
X-CrossPremisesHeadersFiltered: EX10HYB02SAT.usa.ccu.clearchannel.com
X-OrganizationHeadersPreserved: EX10HYB02SAT.usa.ccu.clearchannel.com
X-Proofpoint-Virus-Version: vendor=fsecure engine=2.50.10432:,, definitions=2015-10-12_08:,,
 signatures=0
X-CrossPremisesHeadersFiltered: EX10HUB01.usa.ccu.clearchannel.com
X-OrganizationHeadersPreserved: EX10HUB01.usa.ccu.clearchannel.com
X-Proofpoint-Virus-Version: vendor=fsecure engine=2.50.10432:,, definitions=2015-10-12_08:,,
 signatures=0
X-CrossPremisesHeadersFiltered: EX10HYB01SAT.usa.ccu.clearchannel.com
X-OrganizationHeadersPreserved: EX10HYB01SAT.usa.ccu.clearchannel.com
X-Proofpoint-Virus-Version: vendor=fsecure engine=2.50.10432:,, definitions=2015-10-12_08:,,
 signatures=0
X-CrossPremisesHeadersFiltered: EX10HYB02SAT.usa.ccu.clearchannel.com
X-OrganizationHeadersPreserved: EX10HYB02SAT.usa.ccu.clearchannel.com
X-Proofpoint-Virus-Version: vendor=fsecure engine=2.50.10432:,, definitions=2015-10-12_08:,,
 signatures=0
Amit KumarCommented:
Seems gateway configuration has bad smarthosts or bad configuraiton, because your e-mail is going through below mail hops:

EX10MBX02.usa.ccu.clearchannel.com ([fe80::750c:82c:4337:66cd]) ------>hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com [207.230.136.2]) ------>mx0b-001b1801.pphosted.com ------>pps.filterd (m0077986.ppops.net [127.0.0.1])------>mx0b-001b1801.pphosted.com (8.15.0.59/8.15.0.59)

Now mx0b-001b1801.pphosted.com is again sending same e-mail to hybridhubin.iheartmedia.com (10.121.10.32) -------> hybridhubout.iheartmedia.com (HybridHubOut.iheartmedia.com [207.230.136.2]) -----> mx0a-001b1801.pphosted.com

If you look above logs it is clear mail is routing between same hosts... please check how pphosted is configured to deliver e-mails and how Hybridout is there to send e-mail..
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