Mail goes to junk at outlook.com even do SPF and DKIM passes

[Daniël van Zoelen]

I'am getting no-where with Outlook.com support so I'am trying to get some helpfull information and suggestions from here.

We have an Office 365 business subscription for our own private domain name and my wife's business domain names. She can mail her customers with an email address (via Shared Mailbox) from het business domain name. This mail arrives in the inbox if the customer uses Gmail or another mail provider. However, if the customer uses outlook.com/Hotmail.xom of live.nl, then the mail she send will go to the customers Junk Email folder.

I can reproduce this by sending an e-mail from her business domain to a outlook.com address that I have created for myself.

For my wife's domain name I have setup the correct SPF record and have setup DKIM. The header of the mail going to the spam folder in Outlook.com shows that SPF and DKIM have both passed and are permitting Office365 as legit mail sender for here domain. Still the mail goes to the Junk email folder when the customer uses Outlook.com.

The only thing I can think of is that I used the DKIM 2048 key, Gmail can handle this, but I believe that I read somewhere that outlook.com only supports the 1024 key. Does anybody know if this is correct?

When raising this issue with Outlook.com, they always want to receive the IP address of my mailserver, but like I said our mail is hosted in Office 365. So there default answer pointing me to Smart Network Data Services (SNDS) program and Junk Email Reporting Program (JMRP) have no use because I don't run my own mailserver.

Received-SPF
Pass (protection.outlook.com: domain of <DOMAIN> designates 40.107.1.105 as permitted sender) receiver=protection.outlook.com; client-ip=40.107.1.105; helo=EUR02-HE1-obe.outbound.protection.outlook.com;

ARC-Authentication-Results
i=1; mx.microsoft.com 1; spf=pass smtp.mailfrom=<DOMAIN>; dmarc=pass action=none header.from=<DOMAIN>; dkim=pass header.d=<DOMAIN>; arc=none

[#2]

@Daniël van Zoelen I can't help but just to advise of my experience.  I have a small web design agency and we host all client websites and email.  The problem you highlight has increased recently even though our IP is clean; dkim, SPF and Reverse DNS records have been long set up; and a dmark policy is in place.

Here's the report I got from MS deliverability team: 

"We have reviewed your IP (XX.XXX.XX.XX) and determined that messages are being filtered (i.e. sent to the Junk folder) based on the recommendations of the SmartScreen® Filter.

Email filtering is based on many factors, but primarily it's due to mail content and recipient interaction with that mail.  Because of the proprietary nature of SmartScreen® and because SmartScreen® Filter technology is always adapting and learning more about what is and isn't unwanted mail, it is not possible for us to offer specific advice about improving your mail content. However, in general SmartScreen® Filter evaluates specific words or characteristics from each e-mail message and weights them, based on their likelihood to indicate that a message is unwanted or legitimate mail."  He then goes on to say that our IP cannot be 'mitigates' (whitelisted) at this time.

Frankly SMARTSCREEN is interfering rubbish.  We have many situations where a company has emailed one of our clients and the reply email has been treated as Junk because of SMARTSCREEN.  This is patently ridiculous - how can a reply be junk?

The clients are all small businesses and none of them send bulk mail or do any heavy marketing. The email content is all perfectly legitimate, has no spammy content, and is NOT rejected anywhere else.  I would prefer emails to bounce back - at least you know it hasn't been delivered. With spam things just get missed - important things like sales opportunities, meetings, rescheduled appointments and so on.

Microsoft cannot be unaware of this issue - but they don't seem to be concerned in the slightest.

[#3]

Hi Daniel

I have same issue

Its solved or still?

[#4]

@Daniël van Zoelen I have the same problem with all Microsoft eMail domains. My DMARC (DNS, DKIM and SPF) records are all correct and PASS every other eMail domain in the world. Even the DMARC reports we receive from Microsoft shows that we PASS on all checked parameters, YET our eMail is rejected (550 error) EVERY time I send an eMail to any Microsoft domain. Have you had ANY success in finding anyone at Microsoft that will help? After a year of trying, I am about to call Redmond, WA and speak to a senior IT manager/executive.  HELP! 

[#5]

I am having a direct variation on this problem - my home mail host passes all DMARC/SPF/DKIM signing tests, yet my DMARC return report from MS is always "fail", which makes me believe my mail is landing in peoples junk filter when it should not be..  Very frustrating..

Lines 29 and  30..

What could I possibly do to fix this?

Eric

<?xml version="1.0"?>
<feedback xmlns:xsd="http://www.w3.org/2001/XMLSchema" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
  <version>1.0</version>
  <report_metadata>
    <org_name>Enterprise Outlook</org_name>
    <email>email address removed for privacy reasons</email>
    <report_id>bf2f5c745bc64182a75a1219f0d04feb</report_id>
    <date_range>
      <begin>1679616000</begin>
      <end>1679702400</end>
    </date_range>
  </report_metadata>
  <policy_published>
    <domain>mtrcycllvr.org</domain>
    <adkim>r</adkim>
    <aspf>r</aspf>
    <p>none</p>
    <sp>none</sp>
    <pct>100</pct>
    <fo>0</fo>
  </policy_published>
  <record>
    <row>
      <source_ip>50.43.61.154</source_ip>
      <count>1</count>
      <policy_evaluated>
        <disposition>none</disposition>
        <dkim>fail</dkim>
        <spf>fail</spf>
      </policy_evaluated>
    </row>