E-Mail Delivery Issue Exchange 2010

Seemingly out of nowhere (although I know that is never the case) we are having issues with the delivery of e-mail from specific email servers - GMAIL (and people who use Google Apps for Email) and maybe Office365 senders.  They can send email with no attachments and seemingly attachments up to about 100k or so with no problem.  Any attachments that are bigger than that end up with the failure listed below.  Here's the thing... if I send the SAME e-mail with the SAME attachments from a non-GMAIL or non-Office365 server it flows in without any problem at all.  It seems to only hold up emails from GMAIL/Office365...


Delivery has failed to these recipients or groups:
MyUser (username@mydomain.org)
The server has tried to deliver this message, without success, and has stopped trying. Please try sending this message again. If the problem continues, contact your helpdesk.
Diagnostic information for administrators:
Generating server: CO1PR06MB080.namprd06.prod.outlook.com
Receiving server: na01-internal.map.protection.outlook.com (
Total retry attempts: 256
8/21/2013 8:03:12 PM - Remote Server at na01-internal.map.protection.outlook.com ( returned '550 4.4.7 QUEUE.Expired; message expired'
8/21/2013 7:47:35 PM - Remote Server at na01-internal.map.protection.outlook.com ( returned '451 4.4.0 SMTPSEND.SuspiciousRemoteServerError; remote server disconnected abruptly; retry will be delayed'
Original message headers:
Received: from CO1PR06MB079.namprd06.prod.outlook.com ( by
 CO1PR06MB080.namprd06.prod.outlook.com ( with Microsoft SMTP
 Server (TLS) id 15.0.745.25; Mon, 19 Aug 2013 20:06:32 +0000
Received: from CO1PR06MB079.namprd06.prod.outlook.com ([]) by
 CO1PR06MB079.namprd06.prod.outlook.com ([]) with mapi id
 15.00.0745.000; Mon, 19 Aug 2013 20:06:31 +0000
From: Another Dude <Someone@somewhere.com>
To: "JOtherUser (someone@something.com)" <someone@something.com>
CC: "Username" <username@mydomain.org>
Subject: FW: Redlines
Thread-Topic: Redlines
Thread-Index: Ac6dAeFReQtXlgwbTWy7jl15ygScigACjHkwAAFgqXAAAXfQYA==
Date: Mon, 19 Aug 2013 20:06:31 +0000
Message-ID: <8bc413f15ef443fcbd11cf1b7d7f48e9@CO1PR06MB079.namprd06.prod.outlook.com>
References: <899a5d03a602499bbea3303347c6b12c@BN1PR06MB007.namprd06.prod.outlook.com>
In-Reply-To: <b3a96d4d04754a31a5c29081d02eb84d@BN1PR06MB007.namprd06.prod.outlook.com>
Accept-Language: en-US
Content-Language: en-US
X-MS-Has-Attach: yes
x-originating-ip: []
x-forefront-prvs: 09435FCA72
x-forefront-antispam-report: SFV:NSPM;SFS:(41574002)(199002)(189002)(48214007)(377454003)(54504004)(164054003)(51856001)(19300405004)(74366001)(65816001)(80022001)(59766001)(77982001)(19580395003)(76796001)(76786001)(76576001)(16236675002)(19580385001)(83322001)(81686001)(33646001)(83072001)(81816001)(63696002)(47976001)(50986001)(46102001)(49866001)(47736001)(79102001)(15202345003)(4396001)(81542001)(74316001)(74876001)(69226001)(221733001)(53806001)(54316002)(54356001)(74706001)(66066001)(56816003)(77096001)(80976001)(56776001)(74662001)(74502001)(76482001)(81342001)(31966008)(47446002)(24736002)(80792004);DIR:OUT;SFP:;SCL:1;SRVR:CO1PR06MB080;H:CO1PR06MB079.namprd06.prod.outlook.com;CLIP:;RD:InfoNoRecords;A:1;MX:1;LANG:en;
Content-Type: multipart/mixed;
MIME-Version: 1.0
X-OriginatorOrg: domain.com
Who is Participating?
epohlConnect With a Mentor Commented:
Are you running a Cisco ASA firewall by chance? If so I have seen this issue caused by the SMTP Fixup protocol when using TLS encryption (Office 365 and GMAIL both use it). Try disabling SMTP fixup and see if this resolves your issue.
perktechAuthor Commented:
No, I am running a Watchguard FireboxX1250e.

Any idea how to disable that on the Watchguard?  I'm unfamiliar with "SMTP Fixup"?
I don't use watchguard much but I believe it has something similar where it will be an smtp proxy. Are you using this option to scan emails? If so it might be worth disabling it to see if the problem is with the actual firewall or the exchange server itself. Is there anything else that scans emails on your network?

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perktechAuthor Commented:
It looks like the "BDAT/CHUNKING" setting must be similar -- I googled what you suggested and was pointed to that the ESMTP filter.  I unchecked it and it seems to have fixed the issue.

perktechAuthor Commented:
Good help with it -- wasn't exactly the answer but it pointed me in the direction of the answer.
We had a problem with this error that out of the blue popped up.  We have an ASA and I removed the line "inspect esmtp" from the ASA and the problem went away.  Thanks!
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