Outlook keeps bouncing mail back to me

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timbo1604

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#144258 13-May-2014 08:26

I'm trying to send a pdf attachment in Outlook to Xero, it's only 0.8mb.

Immediately after I send it I get an 'undeliverable' email back, content shown below. Any ideas?

Delivery has failed to these recipients or groups: bankfeeds@xero.com (bankfeeds@xero.com)
Attachment contains an executable Diagnostic information for administrators: Generating server: BLUPR04MB516.namprd04.prod.outlook.com bankfeeds@xero.com
Remote Server returned '550 5.7.1 TRANSPORT.RULES.RejectMessage; the message was rejected by organization policy' Original message headers:

Received: from BLUPR04CA009.namprd04.prod.outlook.com (10.255.219.157) by 
 BLUPR04MB516.namprd04.prod.outlook.com (10.141.29.26) with Microsoft SMTP 
 Server (TLS) id 15.0.944.11; Mon, 12 May 2014 20:18:52 +0000 
Received: from BN1AFFO11FD025.protection.gbl (2a01:111:f400:7c10::152) by 
 BLUPR04CA009.outlook.office365.com (2a01:111:e400:83f::29) with Microsoft 
 SMTP Server (TLS) id 15.0.934.12 via Frontend Transport; Mon, 12 May 2014 
 20:18:51 +0000 
Received: from mail-pa0-f44.google.com (209.85.220.44) by 
 BN1AFFO11FD025.mail.protection.outlook.com (10.58.52.85) with Microsoft SMTP 
 Server (TLS) id 15.0.939.9 via Frontend Transport; Mon, 12 May 2014 20:18:51 
 +0000 
Received: by mail-pa0-f44.google.com with SMTP id ld10so9210073pab.17 
        for <bankfeeds@xero365.onmicrosoft.com>; Mon, 12 May 2014 13:18:50 -0700 (PDT) 
X-Received: by 10.68.224.101 with SMTP id rb5mr282482pbc.135.1399925930660; 
        Mon, 12 May 2014 13:18:50 -0700 (PDT) 
X-Gm-Message-State: ALoCoQmHJWvH6h5uXNz/ 
X-Received: by 10.68.224.101 with SMTP id rb5mr282457pbc.135.1399925930371; 
        Mon, 12 May 2014 13:18:50 -0700 (PDT) 
Received: from col0-omc4-s16.col0.hotmail.com (col0-omc4-s16.col0.hotmail.com. [65.55.34.218]) 
        by mx.google.com with ESMTP id hb8si6851455pbc.325.2014.05.12.13.18.49 
        for <bankfeeds@xero.com>; 
        Mon, 12 May 2014 13:18:50 -0700 (PDT) 
Received-SPF: SoftFail (: domain of transitioning hotmail.com discourages 
 use of 209.85.220.44 as permitted sender) 
Authentication-Results: spf=softfail (sender IP is 209.85.220.44) 
 smtp.mailfrom=timcooke1604@hotmail.com;  
Received: from COL130-W83 ([65.55.34.201]) by col0-omc4-s16.col0.hotmail.com with Microsoft SMTPSVC(6.0.3790.4675); 
	 Mon, 12 May 2014 13:18:49 -0700 
X-TMN: [3AGsnIXL4Tvn00JhpUKNO91/J96I1rOM] 
X-Originating-Email: [timcooke1604@hotmail.com] 
Message-ID: <COL130-W8351F41054DA4AC5CE03A6D1350@phx.gbl> 
Return-Path: timcooke1604@hotmail.com 
Content-Type: multipart/mixed; 
	boundary="_9f29cdb7-ff0a-436e-bc38-12fbdeba4c60_" 
From: Tim Cooke <timcooke1604@hotmail.com> 
To: "bankfeeds@xero.com" <bankfeeds@xero.com> 
Subject: Halo Food Service Ltd 
Date: Tue, 13 May 2014 08:18:49 +1200 
Importance: Normal 
MIME-Version: 1.0 
X-OriginalArrivalTime: 12 May 2014 20:18:49.0560 (UTC) FILETIME=[62AD4D80:01CF6E1F] 
X-EOPAttributedMessage: 0 
X-Forefront-Antispam-Report: 
 CIP:209.85.220.44;CTRY:US;IPV:NLI;IPV:NLI;EFV:NLI;SFV:NSPM;SFS:(SRVR:BLUPR04MB516;H:mail-pa0-f44.google.com;FPR:;MLV:sfv;PTR:mail-pa0-f44.google.com;MX:1;A:1;

I don't know much about anything but I'll give it a go.

Inphinity

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#1042758 13-May-2014 08:29

Are you using Gmails SMTP server with a hotmail account?

timbo1604

102 posts

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#1042760 13-May-2014 08:30

not that I know of, I have a gmail account but never use it.

xpd

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#1042764 13-May-2014 08:40

Somewhere your email is getting delivered by a Google system which is on a blacklist.
Run your headers above through this and you'll see ....

http://mxtoolbox.com/EmailHeaders.aspx

XPD / Gavin

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timmmay

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#1042795 13-May-2014 09:22

Looks like you're sending email from a Microsoft server to a Gmail server, Xero must use Gmail. There's a problem between those companies according to that, Gmail thinks some Microsoft server is a spam host and is rejecting email from it.

Suggest you fax or post the document to Xero, and raise it with them to deal with. I doubt you could get Microsoft/Gmail to change something on your own.

Now that you mention it email from Xero to me was put into my spam folder last week. I use FastMail.fm.

freitasm

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#1042902 13-May-2014 11:21

The message says "Attachment contains an executable" so I'd say Xero is blocking messages with some attachment types.

I don't think it's "Outlook bouncing" but really Xero's mail system bouncing.

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MikeB4

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#1042914 13-May-2014 11:48

The transport rule message indicates that xero have applied firewall rules concerning the type of file being sent. I would suggest contacting Xero's support team to discuss options.

Here is a crazy notion, lets give peace a chance.

HP

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timbo1604

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#1043024 13-May-2014 13:40

Cheers folks.

Well I tried sending the file from my Gmail account to see if it was the MS/Gmail problem, but that bounced back too. Then I converted the file to jpeg and sent it from Outlook which appears to have worked! I logged a fault with Xero and will let them know about it when they contact me.

Thanks for your advice guys, thread closed!

I don't know much about anything but I'll give it a go.