Solved

Unspecified Error (SENT_MESSAGE): Connection timed out

Posted on 2012-03-25
7
2,257 Views
Last Modified: 2012-06-21
Good Morning folks,

I am having some difficulty with an exchange 2007 server, platform is SBS 2008.  Gmail users can not send email to users on this exchange box when attachments are included.

if they just send a plain text email it comes in right away!

after a few days they get a kickback saying "Unspecified Error (SENT_MESSAGE): Connection timed out" and when I pull the exchange logs there was never an attempt to pass the message into the server.  Gmail did not even connect.

the exact message is (edited to remove user emails):
===============================
From: Mail Delivery Subsystem <mailer-daemon@googlemail.com>
Date: Sat, Mar 24, 2012 at 12:23 PM
Subject: Delivery Status Notification (Failure)
To: xxxxx@xxxxxx.com


Delivery to the following recipient failed permanently:

    xxxxx@xxxxxxcontracting.com

Technical details of permanent failure:
Unspecified Error (SENT_MESSAGE): Connection timed out
=================================


I'm at a total loss on this and mxtoolbox says everything is happy.  green checkmarks all across the board, i can't find us on any RBL's and am wondering if anyone else has seen this before?

Many thanks!
Justin
0
Comment
Question by:mrjking2000
[X]
Welcome to Experts Exchange

Add your voice to the tech community where 5M+ people just like you are talking about what matters.

  • Help others & share knowledge
  • Earn cash & points
  • Learn & ask questions
  • 5
7 Comments
 
LVL 15

Assisted Solution

by:Rajkumar-MCITP
Rajkumar-MCITP earned 125 total points
ID: 37763209
did you check the allowed email received limit to your organization? emails from gmail are less than the limit?

for testing send a email from gmail to internal user more than the allowed limit and search the email queue using queue viewer and if it not there, perform a message tracking

On the NDR email received in Gmail, check the email header to know whether the email reached your organization? or the NDR generated from ur exchange or not etc..
0
 
LVL 1

Author Comment

by:mrjking2000
ID: 37763254
incoming and outgoing email limits are 30 MB, the email in question was 2.5 MB in size.  The NDR was not generated from the exchange box.

message tracking doesn't even show the email getting to the exchange server at all.
0
 
LVL 19

Accepted Solution

by:
suriyaehnop earned 375 total points
ID: 37764565
Do you have anti-spam(Mail Gateway) installed between CAS server?
0
Problems using Powershell and Active Directory?

Managing Active Directory does not always have to be complicated.  If you are spending more time trying instead of doing, then it's time to look at something else. For nearly 20 years, AD admins around the world have used one tool for day-to-day AD management: Hyena. Discover why

 
LVL 1

Author Comment

by:mrjking2000
ID: 37765699
there is no anti-spam device before the server, i do have a sonicwall TZ170 doing a very basic gateway level virus scan.  I disabled that on inbound SMTP.  we will see what happens.
0
 
LVL 1

Author Comment

by:mrjking2000
ID: 37765794
UPDATE: i disabled the SMTP service monitoring and my initial test from a gmail account came right in with an attachment, i'm going to let this ride for a few days and see if the problem is resolved.

thanks,
0
 
LVL 1

Author Comment

by:mrjking2000
ID: 37777375
well for now this does seem to be resolved.  i would have never thought that sonicwall was chewing up the traffic.

many thanks!!
0
 
LVL 1

Author Closing Comment

by:mrjking2000
ID: 37777384
thank you both!  I did check the receive connector settings and also make adjustments there, but the total end was the sonicwall which was monitoring SMTP traffic.
0

Featured Post

Forrester Webinar: xMatters Delivers 261% ROI

Guest speaker Dean Davison, Forrester Principal Consultant, explains how a Fortune 500 communication company using xMatters found these results: Achieved a 261% ROI, Experienced $753,280 in net present value benefits over 3 years and Reduced MTTR by 91% for tier 1 incidents.

Question has a verified solution.

If you are experiencing a similar issue, please ask a related question

Suggested Solutions

Find out what you should include to make the best professional email signature for your organization.
This article lists the top 5 free OST to PST Converter Tools. These tools save a lot of time for users when they want to convert OST to PST after their exchange server is no longer available or some other critical issue with exchange server or impor…
To show how to create a transport rule in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Mail Flow >> Rules tab.:  To cr…
The basic steps you have just learned will be implemented in this video. The basic steps are shown to configure an Exchange DAG in a live working Exchange Server Environment and manage the same (Exchange Server 2010 Software is used in a Windows Ser…

739 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question