Question : delay in emails sent from SBS 2003 to *some* outside recipients

alright folks,

i'm both a reader and contributor here at experts-exchange and i'll be the first to step up and say that i'm no exchange professional - i need some help!!  i have a pretty strange issue going on here and i can't seem to put my finger on whether the problem in email delay resides on my SBS 2003 server or if the delay in email is happening somewhere along the way to it's destination.  i've tested my exchange server's ability to send/receive email and the exchange server's peformance by sending emails from and to my server, using gmail.com, yahoo.com and a few other domains to send and receive from - all test's were successful, as all email was sent and received by the server within a few seconds.  however, user's of my domain (ctklaw.com) are stating that email they send to weinsuredocs.com doesn't land in the recipients mailbox until hours later.  i was able to get 2 email headers from the recipients end, 1 header of an email that apparently went through normally and 1 header of an email that was delayed by a few hours.  i'm not too sure how to decipher these email headers and i'm hoping that one of you exchange/dns guru's will be able to tell me what's going on here:

header of email that went through normally:

From: Hettich, Andrea [mailto:AHettich@weinsuredocs.com]
Sent: Friday, February 15, 2008 2:49 PM
To: Curt Booth
Subject: This is the header from an email today that was   not delayed      


Microsoft Mail Internet Headers Version 2.0

Received: from mm13nt.medmutual.weinsuredocs.com ([10.3.1.22]) by MM-XCHG03.medmutual.weinsuredocs.com with Microsoft SMTPSVC(6.0.3790.1830);

             Fri, 15 Feb 2008 11:24:46 -0500

X-eSCM-MailFrom:

Received: from exprod5mx213.postini.com (64.18.0.72)

            by mm13nt.medmutual.weinsuredocs.com (10.50.5.52);

            Fri, 15 February 2008 11:24:45 -0500

Received: from source ([69.2.172.19]) by exprod5mx213.postini.com ([64.18.4.10]) with SMTP;

            Fri, 15 Feb 2008 08:24:37 PST

MIME-Version: 1.0

Content-Type: multipart/alternative;

            boundary="----_=_NextPart_001_01C86FED.4AEC6DC0"

Content-class: urn:content-classes:message

X-MimeOLE: Produced By Microsoft Exchange V6.5.6944.0

Subject: RE: Parker

Date: Fri, 15 Feb 2008 11:10:33 -0500

Message-ID: <45220BBD5887E843AA02C988A608EB9939FA1D@sbserver.CTKLAW.local>

X-MS-Has-Attach:

X-MS-TNEF-Correlator:

Thread-Topic: Parker

Thread-Index: AchuabJmUf3drBOhRI2n3VPdcckW6ABco2CwAATfFyA=

From: "Roy Cowdrey"

To: "Hettich, Andrea" >,

            "Curt Booth"

Cc: "Kristen Nemecek"

X-pstn-neptune: 0/0/0.00/0

X-pstn-levels:     (S:99.90000/99.90000 CV:99.9000 R:95.9108 P:95.9108 M:97.0282 C:98.6951 )

X-pstn-settings: 5 (2.0000:2.0000) s cv gt3 gt2 gt1 r p m c

X-pstn-addresses: from forward (user good) [235/11]

Return-Path: [email protected]

X-OriginalArrivalTime: 15 Feb 2008 16:24:46.0563 (UTC) FILETIME=[47638330:01C86FEF]

 

------_=_NextPart_001_01C86FED.4AEC6DC0

Content-Type: text/plain;

            charset="us-ascii"

Content-Transfer-Encoding: quoted-printable

 

------_=_NextPart_001_01C86FED.4AEC6DC0

Content-Type: text/html;

            charset="us-ascii"

Content-Transfer-Encoding: quoted-printable

 

 

------_=_NextPart_001_01C86FED.4AEC6DC0--


*****************************************************************************************************************************************


header of email that was delayed:  (sent at 2:45pm and received at 7:11pm on 2/13)

From: Hettich, Andrea [mailto:AHettich@weinsuredocs.com]
Sent: Friday, February 15, 2008 3:04 PM
To: Curt Booth
Subject: This was sent at 2:45 p.m. and received at 7:11 p.m. on 2/13...


Microsoft Mail Internet Headers Version 2.0

Received: from mm13nt.medmutual.weinsuredocs.com ([10.3.1.22]) by MM-XCHG03.medmutual.weinsuredocs.com with Microsoft SMTPSVC(6.0.3790.1830);

             Wed, 13 Feb 2008 19:10:56 -0500

X-eSCM-MailFrom:

Received: from exprod5mx247.postini.com (64.18.0.167)

            by mm13nt.medmutual.weinsuredocs.com (10.50.5.52);

            Wed, 13 February 2008 19:10:53 -0500

Received: from source ([69.2.172.19]) by exprod5mx247.postini.com ([64.18.4.10]) with SMTP;

            Wed, 13 Feb 2008 18:10:47 CST

MIME-Version: 1.0

Content-Type: multipart/mixed;

            boundary="----_=_NextPart_001_01C86E78.E4ED27DC"

Content-class: urn:content-classes:message

X-MimeOLE: Produced By Microsoft Exchange V6.5.6944.0

Subject: Parker

Date: Wed, 13 Feb 2008 14:44:49 -0500

Message-ID: <45220BBD5887E843AA02C988A608EB992A2CDB@sbserver.CTKLAW.local>

X-MS-Has-Attach: yes

X-MS-TNEF-Correlator:

Thread-Topic: Parker

Thread-Index: AchueKQu3HNyFKo+TC6XyNatm1QjHg==

From: "Kristen Nemecek"

To: "Hettich, Andrea" >,

            "Bolin, Rick"

Cc: "Michele Urban" ,

            "John Woods" ,

            "Curt Booth"

X-pstn-neptune: 0/0/0.00/0

X-pstn-levels:     (S:99.90000/99.90000 CV: 3.3547 R:95.9108 P:95.9108 M:97.0282 C:98.6951 )

X-pstn-settings: 5 (2.0000:2.0000) s CV gt3 gt2 gt1 r p m c

X-pstn-addresses: from [235/11]

Return-Path: [email protected]

X-OriginalArrivalTime: 14 Feb 2008 00:10:56.0312 (UTC) FILETIME=[11D50380:01C86E9E]

 

------_=_NextPart_001_01C86E78.E4ED27DC

Content-Type: multipart/alternative;

            boundary="----_=_NextPart_002_01C86E78.E4ED27DC"

 

------_=_NextPart_002_01C86E78.E4ED27DC

Content-Type: text/plain;

            charset="us-ascii"

Content-Transfer-Encoding: quoted-printable

 

------_=_NextPart_002_01C86E78.E4ED27DC

Content-Type: text/html;

            charset="us-ascii"

Content-Transfer-Encoding: quoted-printable

 

 

------_=_NextPart_002_01C86E78.E4ED27DC--

------_=_NextPart_001_01C86E78.E4ED27DC

Content-Type: application/octet-stream;

            name="parker ltr to adjusters 2-13.pdf"

Content-Transfer-Encoding: base64

Content-Description: parker ltr to adjusters 2-13.pdf

Content-Disposition: attachment;

            filename="parker ltr to adjusters 2-13.pdf"

 

 

------_=_NextPart_001_01C86E78.E4ED27DC--





any help would be greatly appreciated!!  thank you

Regards,

Jim P.

Answer : delay in emails sent from SBS 2003 to *some* outside recipients

"i'm not entirely sure what a smart host exactly does.  i know that the smtp connector and smtp virtual server work hand in hand to process mail.  what exactly is the difference between using a smart host and not?"

At the moment, you have an SMTP connector which (I expect) is configured to send mail out via DNS. This means your server performs the MX record lookup on the remote domain and directly connects to the recipient's mail server to transmit the message. This works fine when everything - DNS, RDNS, SMTP banners - is set correctly, but if one particular recipient or other product decides to look up a particular record or piece of information which does not correlate with everything else, the message will usually be rejected. Alternatively, although it is rare, what could be happening here is the message is queued just in case the record is on a server or somewhere which may come back online within a matter of hours. It could be it then times out, but rather than reject the message it is configured to transmit it to the delivery queue anyway. I've never seen this but it could be a plausible explanation.

By using a smart host, you effectively change the settings of the SMTP connector to transmit the mail to an SMTP server at your ISP/host/other service offering SMTP mail transmission. In effect, the Exchange server acts like an Outlook client - it transmits all messages off to a remote server which is then responsible for delivery of the message. By doing this with the larger ISPs, you are virtually (99.9% I suppose) guaranteed they are going to have all the appropriate settings, records and other configuration, in order for other mail servers to accept their mail.

I thought you could temporarily change your mail delivery over to smart host-based and see if the messages get through any quicker. That would isolate whether the problem is with something at your end (if the message went through immediately and this keeps happening time and time again) or still with Postini or another portion of the recipient's end (if it is still delayed, it is highly unlikely that it is your end).

-tigermatt
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