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I am having major issues sending from my SBS2011 machine to Message labs server-13.tower-134.messagelabs.com #553-Message filtered. Refer to the Troubleshooting page at 553-http://www.symanteccloud.com/troubleshooting for more 553 information. (#5.7.1) ##

I have changed the IP and hostnames from the below.

I am not on any IP or domain blacklists.

I have setup SPF (which includes mailchimp servers): v=spf1 mx a ip4:95.74.157.22/32 a:remote.mydomain.com include:servers.mcsv.net ~all

I am sure i have setup my HELO names correctly under the Exchange Management console, sending a test email from the SBS server and looking at the header shows the following:

X-Orig-To: test@testrecepient.com
X-Originating-Ip: [95.74.157.22]
Received: from [95.74.157.22] ([95.74.157.22:52194] helo=remote.mydomain.com)   by
 smtp50.gate.ord1a.rsapps.net (envelope-from <me@mydomain.com>) (ecelerity
 2.2.3.49 r(42060/42061)) with ESMTP    id 11/90-10010-E529C835; Mon, 02 Jun 2014
 11:04:09 -0400
Received: from MYSBSSVR.mydomain.local ([fe80::3159:95a6:23f:1bef]) by
 MYSBSSVR.mydomain.local ([fe80::3159:95a6:23f:1bef%10]) with mapi id
 14.01.0438.000; Mon, 2 Jun 2014 19:03:56 +0400

Is is the main helo name there OK and do i need to worry about the second Received block where the MYSBSVR.mydomain.local is mentioned?

I have asked the ISP to set the reverse DNS for my IP to remote.mydomain.com but they have instead put remote.MYDOMAIN.com - would this case cause HELO lookups to classify this as not matching?

Anything else I can do to find out why i am being filtered?

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1  
DNS and RDNS are case insensitive, whether that insensitivity extends to mail filtering software, I hesitate to say. –  NickW Jun 2 at 16:05

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