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5.4.7 - Delivery expired (message too old) [Default] '[Errno 54] Connection reset by peer'

Posted on 2011-03-25
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Last Modified: 2013-02-13
Is there a non-technical way to tell me how I can direct my client who gets the 5.4.7 - Delivery expired (message too old) [Default] '[Errno 54]
Connection reset by peer'
message when she is trying to send me an email with jpeg attachment (usually it is a large file--10-15 MB when this happens).
I need to tell her IT people what to explore, as I believe it is a problem on their end, not with my server.
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Question by:judysweeney
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Expert Comment

by:AustinComputerLabs
ID: 35216702
Can you post the entire NDR message?
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Author Comment

by:judysweeney
ID: 35216716
The following message to <judy@sweeneyads.com> was undeliverable.
The reason for the problem:
5.4.7 - Delivery expired (message too old) [Default] '[Errno 54]
Connection reset by peer'

The IP address of the MTA to which the message could not be sent:
72.167.238.201

---------- A copy of the message begins below this line ----------
X-IronPort-AV: E=Sophos;i="4.63,237,1299477600";
  d="doc'32?jpg'32,145?scan'32,145,32,145,208,217";a="40027972"
Received: from unknown (HELO usnsh-s-ss40.int.dir.willis.com)
([10.66.195.155])
 by usnsh-s-ip2.willis.com with ESMTP/TLS/DHE-RSA-AES256-SHA; 24 Mar
2011 10:18:32 -0500
Received: from usnsh-i-ex54.int.dir.willis.com
(usnsh-i-ex54.int.dir.willis.com [10.66.20.104]) by
usnsh-s-ss40.int.dir.willis.com (RSA Interceptor) for
<judy@sweeneyads.com>; Thu, 24 Mar 2011 10:25:26 -0500
Received: from USNSH-I-EC30.int.dir.willis.com ([10.66.20.30]) by
usnsh-i-ex54.int.dir.willis.com with Microsoft SMTPSVC(6.0.3790.4675);
       Thu, 24 Mar 2011 10:25:25 -0500
X-MimeOLE: Produced By Microsoft Exchange V6.5
Content-class: urn:content-classes:message
MIME-Version: 1.0
Content-Type: multipart/mixed;
      boundary="----_=_NextPart_001_01CBEA37.B1506011"
Subject: Invitation
Date: Thu, 24 Mar 2011 10:25:11 -0500
Message-ID:
<F46665F76EC17A47B54158C02EAE2A2A037D43A7@USNSH-I-EC30.int.dir.willis.co
m>
X-MS-Has-Attach:
X-MS-TNEF-Correlator:
Thread-Topic: Invitation
Thread-Index: AcvqN6kM4LgZJOHeRVqes2QaERn45Q==
From: "Harris, Nancy" <nancy.harris@willis.com>
To: "Judith Sweeney" <judy@sweeneyads.com>
Cc: "Callen, Paulette" <Callen_Pa@willis.com>
X-OriginalArrivalTime: 24 Mar 2011 15:25:25.0379 (UTC)
FILETIME=[B2C8B530:01CBEA37]
X-RSA-Inspected: yes
X-RSA-Classifications: public
X-RSA-Action: allow
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LVL 13

Expert Comment

by:AustinComputerLabs
ID: 35216829
Reverse DNS for 10.66.195.155 fails and is blacklisted on some lists.
http://multirbl.valli.org/lookup/10.66.195.155.html

Received: from unknown (HELO usnsh-s-ss40.int.dir.willis.com)
([10.66.195.155])


Is willis.com the senders address?
It appears the HELO from "usnsh-s-ss40.int.dir.willis.com" is reporting its' IP is 10.66.195.155. That is a private range. I believe the HELO should be reporting its' IP as the WAN IP that has a reverse DNS setup.
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Author Comment

by:judysweeney
ID: 35217134
willis.com IS the senders address.

So should I take the information below and pose it to their IT people as a possible solution? I am a graphic artist, and I don't want to appear unknowledgeable ...but this is totally out of my league.
You would agree that it is a problem with their server...not on my end?

It appears the HELO from "usnsh-s-ss40.int.dir.willis.com" is reporting its' IP is 10.66.195.155. That is a private range. I believe the HELO should be reporting its' IP as the WAN IP that has a reverse DNS setup.
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LVL 13

Expert Comment

by:AustinComputerLabs
ID: 35217664
Yes, It appears to be an issue with the configuration on their mail server.
For security reasons many mail servers will not accept mail from a server that does not have a valid reverse DNS and a private IP in its' HELO.

If you recieve mail from them without attachments then this is not the issue, even though it is an incorrect setup.
If you are able to receive mail from them without attachments, then your mail server may not allow email of that size.
Are able to recieve email of that size from other clients?
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Author Comment

by:judysweeney
ID: 35219011
My other clients only have limited sending capabilities, so I dont get large emails from them. But I did a test with my email server Go daddy and they were able to send thru a 20 mg file no problem. I feel like I am still not able to take a qualified stand on whether they have the problem or I do. Any further comments? I appreciate our thoughts thus far. Also. I use apple mail as my mail app. I don't think that has anything to do with it right?
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LVL 13

Expert Comment

by:AustinComputerLabs
ID: 35219859
I was able to very quickly find basic errors in their setup and if other clients are able to send large file that rules you out for the most part, other than your mail server may require basic reverse DNS be in place (as it should).
Can you recieve any mail from that client?
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Author Comment

by:judysweeney
ID: 35219914
I receive normal email from that client every day and attachments around 2-8 mg. It's when they get into larger attachments that they get this error message (they would like to send jpegs up to 20 MB). I have been assured by go daddy that I have 30 MB capacity for incoming email.
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LVL 13

Accepted Solution

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AustinComputerLabs earned 250 total points
ID: 35220022
Email is not a very good method for sending large files in general. Have you looked into web disks? Like Jungle Disk. FTP is the best but it requires a client that has and can use an FTP client.

Since the issue is only present with larger files it is probably a time out issue, probably difficult to track down, but if Godaddy had this issue many people would be complaining to GoDaddy. I just did a search for the error and Godaddy and nothing.
I have a web design and computer support company and as such I need ot have a setup that even the most stubborn client can use. I have an FTP server for most clients and Jungle disk for the less adept.
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