Spam false positives.

I got word that a user was not receiving email and attempts to send to him were bouncing. I see why the email was considered spam is due to the following report. Please help me understand, or clarify, the bounced email was generated from outlook / IP:, correct? This is not our server, my understanding Outlook likely Office365 caused the flag.

spam report
LVL 17
WORKS2011Austin Tech CompanyAsked:
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WORKS2011Austin Tech CompanyAuthor Commented:
Concern is my client feels our spam filter is the culprit and doesn't understand why emails cannot be added to the "allow list". Before I explain it's not rejected on our end would like some clarification from EE.

Thank you.
JohnBusiness Consultant (Owner)Commented:
The IP above is Microsoft -

Microsoft Corporation
One Microsoft Way
United States

Microsoft Routing, Peering, and DNS
Quamara, Divya

Microsoft Abuse Contact

Created: 1998-07-10
Updated: 2015-09-29

Completed at 10/19/2015 11:16:11 PM
Processing time: 0.53 seconds
View source

The email is definitely coming from Microsoft, but I do not know why you cannot add it to an allow list. I get mail from Microsoft with no issue.

The email itself may be bad (have bad content).

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User uses web interface to view/send.  Look at account properties dealing with spam handling is it might be too aggressive catching false positives.
Bayes is a content statistical analysis type filter and should include a method by which it can be retrained to not count the message in question as spam or even disable/make the filter less sensitive.

Where are you looking at these statistics? Is this a third party application?
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WORKS2011Austin Tech CompanyAuthor Commented:
Thank you John and arnold.

John, do you feel it's Microsoft's side doing the flagging. We get email from people using Office 365 all the time, I'm assuming it's Office 365. However this one client seems to report bounced emails coming back to them from us. Odd they won't send us a NDR.

arnold, my client does use a spam filter and where this message comes from. I'm trying to determine if our filter is reporting why the sender rejected it. Our filter is setup with their name on the allow list. They claim some emails don't make it.
The message you posted to a rejection because of bayes which is a content filter. You have to look at your email handling and whether the check for the sender is evaluated before the rest and adding the sender there will accept the message before the content filter is applied.  In your current setup when a spam is determined to be spam, the sending server seems to be getting the permanent error response 550.

Given you have the information before, receiving the NDR is unnecessary as you have confirmation of the incoming email being rejected by your setup.

Check what options do you gave, having the setup rejecting the sender message is a final, see if you have a quaranteen option meaning the message is accepted, placed in a spam pan and the recipient notified. The recipient is provided with an option to view the message if they choose, and also have an option to indicate that the message should not have registered as spam.
This will retrain the bayes filtering mechanism.
WORKS2011Austin Tech CompanyAuthor Commented:
appreciate it!!!
JohnBusiness Consultant (Owner)Commented:
@WORKS2011  - You are very welcome and I was happy to help.
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