SBS2008 Mail delivery delays

I have a small network with a single SBS 2008 server running exchange.  Recently we are having issues with mail not being recieved until several hours after it was sent by outside senders.  For the most part, internal e-mail within the exchange organization is working OK.  It seems to be only happening with external messages.  Do you have any suggestions for tracing this issue down???

Any assistance would be appreciated.
ericbeckerditeAsked:
Who is Participating?
 
NarendraGCommented:
I TRIED TELNETTING YOUR SMTP SERVER  BUT UNFORTUNATELY I COULDNT CONNECT

I SUSPECT PROBLEM IN YOUR FIREWALL R WITH YOUR SPAM SECURITY SOFTWARE

0
 
NarendraGCommented:
OK LETS START
https://www.testexchangeconnectivity.com/

RUN IT FROM YOUR SERVER TEST INBOUND CONNECTION

POST RESULT HERE PLEASE

Thanks
0
 
NarendraGCommented:
check it also

1. too big mailbox (entourage is poor handling mailboxes over 500MB)
2. some server ip-address resolving issue
3. SSL enabled on client, but not server
0
Creating Active Directory Users from a Text File

If your organization has a need to mass-create AD user accounts, watch this video to see how its done without the need for scripting or other unnecessary complexities.

 
ericbeckerditeAuthor Commented:
Here is the result of the test.  I see there is a connectivity issue, but messages do come thru (usually only in the evenings).  Please let me know what suggestions you have, and I will continue to work with it.

Testing Inbound SMTP Mail flow for domain beckerdite@mcdormanlawoffice.com
 Failed to test inbound SMTP mail flow.
 Test Steps
 Attempting to retrieve DNS MX records for domain mcdormanlawoffice.com
 Successfully retrieved one or more MX records from DNS
 Additional Details
 MX Records Host mail.mcdormanlawoffice.com, Preference 10


Testing Mail Exchanger mail.mcdormanlawoffice.com.
 One or more SMTP tests failed for this Mail Exchanger.
 Test Steps
 Attempting to resolve the host name mail.mcdormanlawoffice.com in DNS.
 Host successfully resolved
 Additional Details
 IP(s) returned: 69.151.12.186

Testing TCP Port 25 on host mail.mcdormanlawoffice.com to ensure it is listening and open.
 The specified port is either blocked, not listening, or not producing the expected response.
  Tell me more about this issue and how to resolve it
 Additional Details
 The connection was established but a banner was never received.
0
 
ericbeckerditeAuthor Commented:
Not sure if this is related, but I just went into IIS manager to poke around, and when I clicked the + sign to expand Exchange, I get the following error: "Could not find a part of the path '\\.\BackOfficeStorage\domainname\mbx'.
0
 
NarendraGCommented:
i tried again i am able to connect but no banner

try from your internal network

let me know the result
0
 
ericbeckerditeAuthor Commented:
I could telnet my server from within my network using command: telnet localhost 25 yesterday, but at the moment, it won't connect.

I just tried again, and it connected, but no banner.  Then tried again, and didn't connect.

Seems to be intermittent.
0
 
NarendraGCommented:
You have to look at the SMTP headers of the message to see where the delay took place. Message tracking can also show you where the message came in to the system.
0
 
NarendraGCommented:
if possible post  delayed message header here
0
 
NarendraGCommented:
hope there is no delay in internal mails rite?
0
 
ericbeckerditeAuthor Commented:
Here's the header of a message that was sent before 8AM this morning and just received at 1:17PM.  As far as we can tell, internal mails seem to be working OK.

Received: from TX2EHSOBE004.bigfish.com (65.55.88.12) by
 mail.mcdormanlawoffice.com (192.168.0.10) with Microsoft SMTP Server (TLS) id
 8.1.393.1; Fri, 8 Jan 2010 13:16:59 -0600
Received: from mail86-tx2-R.bigfish.com (10.9.14.240) by
 TX2EHSOBE004.bigfish.com (10.9.40.24) with Microsoft SMTP Server id
 8.1.340.0; Fri, 8 Jan 2010 13:45:48 +0000
Received: from mail86-tx2 (localhost.localdomain [127.0.0.1])      by
 mail86-tx2-R.bigfish.com (Postfix) with ESMTP id D8E6E11103F1      for
 <westervelt@mcdormanlawoffice.com>; Fri,  8 Jan 2010 13:45:47 +0000 (UTC)
X-SpamScore: -29
X-BigFish: VPS-29(zza0dJe66R9371Pe2eRzz1202hz31izz2dh54h6bh61h)
X-Spam-TCS-SCL: 0:0
Received: from mail86-tx2 (localhost.localdomain [127.0.0.1]) by mail86-tx2
 (MessageSwitch) id 1262958343634393_17975; Fri,  8 Jan 2010 13:45:43 +0000
 (UTC)
Received: from TX2EHSMHS033.bigfish.com (unknown [10.9.14.245])      by
 mail86-tx2.bigfish.com (Postfix) with ESMTP id 2BE3DFE804F      for
 <westervelt@mcdormanlawoffice.com>; Fri,  8 Jan 2010 13:45:43 +0000 (UTC)
Received: from DSVPWM10.deluxe.com (209.37.138.50) by TX2EHSMHS033.bigfish.com
 (10.9.99.133) with Microsoft SMTP Server (TLS) id 14.0.482.32; Fri, 8 Jan
 2010 13:45:41 +0000
Received: from DSVPWM14C.deluxe.com ([10.102.32.46]) by DSVPWM10.deluxe.com
 ([10.102.32.42]) with mapi; Fri, 8 Jan 2010 07:45:40 -0600
From: "HILL, GAIL" <Gail.Hill@deluxe.com>
To: "'westervelt@mcdormanlawoffice.com'" <westervelt@mcdormanlawoffice.com>
Date: Fri, 8 Jan 2010 07:45:40 -0600
Subject: One more question?? I did not receive your fax - please re-fax
 800-447-1407
Thread-Topic: One more question?? I did not receive your fax - please re-fax
 800-447-1407
Thread-Index: AcqQZUQQGfVOn/GXQ8SeQZn+QkSQxwAA4F+w
Message-ID: <2F07AC06E1F7E44D872B66053BB530F96FBA61009D@DSVPWM14C.deluxe.com>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach: yes
X-MS-TNEF-Correlator:
acceptlanguage: en-US
Content-Type: multipart/related;
      boundary="_004_2F07AC06E1F7E44D872B66053BB530F96FBA61009DDSVPWM14Cdelu_";
      type="multipart/alternative"
MIME-Version: 1.0
X-Reverse-DNS: mtaout1.deluxe.com
Return-Path: Gail.Hill@deluxe.com
X-MS-Exchange-Organization-PRD: deluxe.com
X-MS-Exchange-Organization-SenderIdResult: None
Received-SPF: None (APPSERVER.lawoffice.local: Gail.Hill@deluxe.com does not
 designate permitted sender hosts)
X-MS-Exchange-Organization-SCL: 4
X-MS-Exchange-Organization-PCL: 2
X-MS-Exchange-Organization-Antispam-Report:
 DV:3.3.5705.600;SID:SenderIDStatus
 None;TIME:TimeBasedFeatures;OrigIP:65.55.88.12
0
 
ericbeckerditeAuthor Commented:
I had already tried disabling my spam filter/security software, and that didn't help, but I went ahead and completetly uninstalled it, and everything seems to be working now!  I will try reinstalling it to see if it "breaks" again.
0
Question has a verified solution.

Are you are experiencing a similar issue? Get a personalized answer when you ask a related question.

Have a better answer? Share it in a comment.

All Courses

From novice to tech pro — start learning today.