Good day,
In our web service we're developing bulk email messages sending feature and also we'd like to support bulk messaging through office365. But on early stages of testing we've faced with spam abuse issue and it is presented even on sending of single message. While sending email (through outlook.office365.com) works ok from localhost, sending message from one of our staging environments (basically some Linux VM in AWS cloud) triggers next response from mail server:

Delivery has failed to these recipients or groups:

anton@nimble.com
Your message wasn't delivered because the recipient's email provider rejected it.









Diagnostic information for administrators:
Generating server: BN3PR0701MB1156.namprd07.prod.outlook.com
anton@nimble.com
Remote Server returned '550 5.7.501 Access denied, spam abuse detected. 
For more information please go to 
http://go.microsoft.com/fwlink/?LinkId=526653'
Original message headers:
Authentication-Results: nimble.com; dkim=none (message not signed)
 header.d=none;
Received: from tb1.devnimble.com (54.188.250.107) by
 BN3PR0701MB1156.namprd07.prod.outlook.com (10.160.114.16) with Microsoft SMTP
 Server (TLS) id 15.1.231.21; Wed, 12 Aug 2015 11:20:40 +0000
Content-Type: multipart/mixed;
	boundary="===============2846377685716320236=="
MIME-Version: 1.0
From: <admin@nimbleinc.onmicrosoft.com>
To: <anton@nimble.com>
Date: Wed, 12 Aug 2015 11:20:36 +0000
Subject: hello subject
X-Originating-IP: [54.188.250.107]
X-ClientProxiedBy: CY1PR17CA0001.namprd17.prod.outlook.com (25.163.68.11) To
 BN3PR0701MB1156.namprd07.prod.outlook.com (25.160.114.16)
Return-Path: admin@nimbleinc.onmicrosoft.com
Message-ID:
	<BN3PR0701MB11563C3E6C1A4464C15A5E44E47E0@BN3PR0701MB1156.namprd07.prod.outlook.com>
X-Microsoft-Exchange-Diagnostics:
	1;BN3PR0701MB1156;2:MQH2Q2Cnrb/kovuCcUTr4NLd3sem+GhcmrmVxNVKLl5ciem76Kp4XG39Q2x/mPJ+dAP79+FNNWHZE+J0Vx5wKik+3IhjCwJHMjEpgpYOmSIbDZbgUmFvXIANHZJXcu7vPQkhize4xgHsawfDLfXFIcPMB6zEEaBmov1O97682cA=;3:BfsnyIvTk+ELLfgUXXU9yc9yRCfFohJjforhly6dBY52U6aSVwxzOuUlecnjwLySnKiSOIcXfagHNFTokr/IVYNUc/qx+rahdmY8diWYU/i6xPr2kGFzEoP4KnvU0YQS6R2e9NDnAcGpLz1vpNcgdg==;25:SISDEXcQ51Kw4xWGlxD3I+Qzvjo3gjCxzj7RZNET0XTUFXaAixlF18aPyQRNZ64aC8atBqaHdVBzl4qip5bMc1K0KAt0ujTdbbmPWSZ4Nk/C9GX7KAYo00sP0PrIBfG6HqWjBo3VcdqjlznLKM22fw==;4:XQqOMEoRZfraW4R+wu8sQI3XnUbFooyBYroZ9zex61TGhlwunZHbvIUBLxzxpIUBkskJ9it1CYE/KEXhLgFEfrqYsT4p8K+E6jSAHyJbp++c1Zb3Iwf+uK5TSFDUPpD63h8g0yT6WSi8R6pothbkCo2cIXGtGYWL1Qcx6ZzqbBElkVKFaiVZbRU++GXWNvgPkC4GaSt66JDiydNAwLCPgw==;23:VUATg1SwSGwLS5hBbbUx+mLXoUPhr5KglwDGs96KlqKU6eQZHrSnNKa2oXb0bRzS/Wib6Kga8RwExhNuFek2FXmSeJRc7WHRWRMUTaLPpU1oJMTiXMwUT+xeUdXYGe1YBGKQLBy3vJzNtQL8x9g8bm/0kBqDOQFXUDDfiSQUFFBRqXf0pwB0J+PRSuTtY30vfIqbJK0OVMmhlEPIGi5iq2YZWFOVy2l8g3/ttumBxiM=
X-Microsoft-Antispam: UriScan:;BCL:0;PCL:0;RULEID:;SRVR:BN3PR0701MB1156;
X-Microsoft-Antispam-PRVS:
	<BN3PR0701MB11569718257610FFE1499A3AE47E0@BN3PR0701MB1156.namprd07.prod.outlook.com>
X-Exchange-Antispam-Report-Test: UriScan:;
X-Exchange-Antispam-Report-CFA-Test:
	BCL:0;PCL:0;RULEID:(601004)(5005006)(3002001)(6000006);SRVR:BN3PR0701MB1156;
X-Forefront-PRVS: 0666E15D35

According to https://technet.microsoft.com/en-us/library/dn205071(v=exchg.150).aspx - antispam headers are good. Can it be than Exchange treated this email like spam,  because of suspicious hostname tb1.devnimble.com (which is not visible outside of our vpn)?
Maybe you can suggest some good rules of using Office365 SMTP server for sending messages on behalf of user and sending them not from one machine but rather from distributed web service?

Microsoft doesn't share technical details their antispam measures, so I'm afraid that nobody can or will answer that, sorry.

Microsoft doesn't share technical details about their antispam measures, so I'm afraid that nobody can or will answer th

There are tons of similar issues reported on the O365 community forums. Best thing to do is open a case with O365 support, escalating to the EOP team should take care of this.

Hi,

O365 community forum is a better place to post for your situation.

Forum link: https://community.office365.com/en-us/

Best Regards.