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Exchange E-mail issue

S

Skylinerecording

Weaksauce
Joined
Oct 15, 2007
Messages
116
I'm experiencing a weird issue with my exchange server. We can send e-mail perfectly fine and receive most email perfectly fine. The issue i'm having is most e-mail coming from a rr.com so road runner e-mail and most e-mail coming from juno.com accounts aren't coming through or show up a good time after being spent. After checking the spam filter logs on my firewall I can see the e-mails are coming into the network fine but what I've noticed is the same e-mail will be sent to the server roughly 6 times every 5 mins or so and after the 6th time the e-mail will actually show up. And i've tested this on a few exchange servers and it seems to be on issue on all of them. Now if I send from gmail, yahoo or another exchange server at a different company they come through fine and show up with in a min or so. Also the other issue i've seen is the header is completely different on rr.com emails then e-mails from yahoo or gmail.


I've attached what the header says on rr.com e-mails.

Received: from cdptpa-queue03.email.rr.com (107.14.166.226) by
mail.domain.com (x.x.x.x) with Microsoft SMTP Server id 14.1.438.0;
Wed, 6 Nov 2013 22:14:36 -0500
Received: from cdptpa-oedge-vip.email.rr.com ([107.14.174.243]) by
cdptpa-queue03.email.rr.com (InterMail vM.8.04.01.11
201-2343-100-164-20130125) with ESMTP id
<20131107031428.LDSP26149.cdptpa-queue03.email.rr.com@cdptpa-oedge-vip.email.rr.com>
for <user@domain.com>; Thu, 7 Nov 2013 03:14:28 +0000
Return-Path: <user@rochester.rr.com>
Authentication-Results: cdptpa-oedge02 smtp.user=user@rochester.rr.com; auth=pass (LOGIN)
Received: from [107.14.174.248] ([107.14.174.248:3304] helo=cdptpa-web21) by
cdptpa-oedge02 (envelope-from <user@rochester.rr.com>) (ecelerity
3.5.0.35861 r(Momo-dev:tip)) with ESMTPA id 5D/6A-27821-1CFFA725; Thu, 07 Nov
2013 02:49:37 +0000
Message-ID: <20131107024937.K7Q7L.17859.root@cdptpa-web21>
Date: Thu, 7 Nov 2013 02:49:37 +0000
From: <user@rochester.rr.com>
To: <user@domain.com>
Subject: One last email test
MIME-Version: 1.0
Content-Type: text/plain; charset="utf-8"
Content-Transfer-Encoding: 7bit
X-Priority: 3 (Normal)
Sensitivity: Normal
X-Originating-IP: from 74.74.216.168 by webmail.rochester.rr.com; Thu, 7 Nov 2013 2:49:37 +0000
X-RR-Connecting-IP: 107.14.168.130:2525
X-Cloudmark-Score: 0
X-MS-Exchange-Organization-AuthSource: server.domain.local
X-MS-Exchange-Organization-AuthAs: Anonymous
X-MS-Exchange-Organization-PRD: rochester.rr.com
X-MS-Exchange-Organization-SenderIdResult: Pass
Received-SPF: Pass (server.domain.local: domain of
user@rochester.rr.com designates 107.14.166.226 as permitted sender)
receiver=server.domain.local; client-ip=107.14.166.226;
helo=cdptpa-queue03.email.rr.com;
X-MS-Exchange-Organization-SCL: 3
X-MS-Exchange-Organization-PCL: 2
X-MS-Exchange-Organization-Antispam-Report:
DV:3.3.12819.480;SID:SenderIDStatus Pass;OrigIP:107.14.166.226



I did changed the domain name of my clients network and also any IP's relating to it and also changed the name of the road runner user but I left the road runner ip's unchanged. Any insight would be much appreciated. I'm at a loss right now.


Just did some more testing this issue is only happening in SBS 2011 installs that use exchange 2010. I tried an SBS 2008 box that uses exchange 2007 and the e-mail went through perfectly fine on the first try.
 
Last edited:
Everything looks ok. I did notice your time stamps are kind of whacky (check your time). I know some ISP throttle port 25 as well. I've come up with a similar issue on one of my server. I disabled spam filtering inside exchange entirely bounce the Exchange topology and try again.

Also if you are using FW to spam filter check your RBL.
SBS can be finicky I found troubleshooting can cause issue best thing do is re-run the wizard for domain.

Also how does email flow FW->SBS? Any smart hosts ?
 
Yea it goes FW then SBS no smart host. I've been wondering if maybe the ISP was doing something but if that was the case it would make this problem even weirder our ISP is time warner and it's their hosted e-mails that we are having trouble with.

I have heard time warner's been getting black listed a lot lately but my FW spam filter gives it a negative rating and it's odd that after the 5th or 6th time the email sends back it actually comes through.
 
What do the inbound logs on the Exchange SMTP server show? By default, the logs are here:

%ProgramFiles%\Microsoft\Exchange Server\TransportRoles\Logs\ProtocolLog\SmtpReceive
 
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