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102 posts

Master Geek
+1 received by user: 1

Topic # 144258 13-May-2014 08:26
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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: (
Attachment contains an executable Diagnostic information for administrators: Generating server:
Remote Server returned '550 5.7.1 TRANSPORT.RULES.RejectMessage; the message was rejected by organization policy' Original message headers:


Received: from ( by ( with Microsoft SMTP


Server (TLS) id 15.0.944.11; Mon, 12 May 2014 20:18:52 +0000


Received: from (2a01:111:f400:7c10::152) by (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 ( by ( with Microsoft SMTP


Server (TLS) id 15.0.939.9 via Frontend Transport; Mon, 12 May 2014 20:18:51




Received: by with SMTP id ld10so9210073pab.17


for <>; Mon, 12 May 2014 13:18:50 -0700 (PDT)


X-Received: by with SMTP id rb5mr282482pbc.135.1399925930660;


Mon, 12 May 2014 13:18:50 -0700 (PDT)


X-Gm-Message-State: ALoCoQmHJWvH6h5uXNz/


X-Received: by with SMTP id rb5mr282457pbc.135.1399925930371;


Mon, 12 May 2014 13:18:50 -0700 (PDT)


Received: from ( [])


by with ESMTP id hb8si6851455pbc.325.2014.


for <>;


Mon, 12 May 2014 13:18:50 -0700 (PDT)


Received-SPF: SoftFail (: domain of transitioning discourages


use of as permitted sender)


Authentication-Results: spf=softfail (sender IP is;


Received: from COL130-W83 ([]) by with Microsoft SMTPSVC(6.0.3790.4675);


Mon, 12 May 2014 13:18:49 -0700


X-TMN: [3AGsnIXL4Tvn00JhpUKNO91/J96I1rOM]


X-Originating-Email: []


Message-ID: <COL130-W8351F41054DA4AC5CE03A6D1350@phx.gbl>




Content-Type: multipart/mixed;




From: Tim Cooke <>


To: "" <>


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







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Uber Geek
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  Reply # 1042758 13-May-2014 08:29
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Are you using Gmails SMTP server with a hotmail account?

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102 posts

Master Geek
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  Reply # 1042760 13-May-2014 08:30
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not that I know of, I have a gmail account but never use it.



The Overrated Raccoons
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  Reply # 1042764 13-May-2014 08:40
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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 ....

XPD / Gavin / DemiseNZ


For Free Games, Geekiness and Reviews, visit :


Home Of The Overrated Raccoons


Battlenet : XPD#11535    Origin/Steam/Epic/Uplay : xpdnz


Sea of Thieves Down Under

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  Reply # 1042795 13-May-2014 09:22
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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

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  Reply # 1042902 13-May-2014 11:21
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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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  Reply # 1042914 13-May-2014 11:48
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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.

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The views stated in my posts are my personal views and not that of any other organisation.


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102 posts

Master Geek
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  Reply # 1043024 13-May-2014 13:40
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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!

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