Mailing-List: contact users-help@spamassassin.apache.org; run by ezmlm
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Subject: Re: OT - Hotmail/Outlook.com marking most of our email as Junk
To: users@spamassassin.apache.org
References: <e0e87cbc-23ff-6af8-967c-8a72150be675@open-t.co.uk>
From: G Roach <groachmail-2012@yahoo.com>
Message-ID: <c35b3edd-7623-2c91-346f-c0a1a0232d47@yahoo.com>
Date: Tue, 19 Sep 2017 07:44:38 +0100
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Microsoft use their own methods of detection including based on 
reputation and 'length of service' - ie, if you have only just started 
sending emails out from your own address (which you have) then they may 
well consider you suspicious. Theres not much yo can do about it.   More 
info here: https://mail.live.com/mail/troubleshooting.aspx


On 19/09/2017 07:25, Sebastian Arcus wrote:
> This is a bit off topic as it is not directly related to SA, but I'm 
> hoping that with the email and spam expertise on this group, someone 
> might throw in a useful idea - which would be much appreciated.
>
> I have this problem on one site where most emails we send to 
> Hotmail/Outlook.com/Live.com email addresses end up in Junk at the 
> recipient's end. Things I have tried:
>
> 1. I've setup SPF, DKIM, DMARC (and set it to 'reject').
>
> 2. We used to smart relay outbound email through the hosting provider 
> (1and1), but now changed to send directly from our own IP address, so 
> that we can control the reputation of the sending IP - no change.
>
> 3. I've checked our public IP and the domain name at mxtoolbox.com - 
> all tests pass (the public IP has been delisted from the Spamhaus 
> non-MX/end-user IP database).
>
> 4. I've setup forward and reverse DNS entries for our IP address.
>
> 5. I've checked with all DNS blocklists/blacklists I could find - our 
> domain or IP address is not flagged up anywhere.
>
> 6. This is a small network which I've been managing for years - the 
> domain name has not been used to send marketing/lists email of any 
> sort - so the historic reputation should be fine.
>
> 7. I've setup a monitor and block on port 25 outbound on the network 
> firewall - in case there is a trojan on a machine on the network 
> sending out spam and ruining the reputation of our IP - it's never 
> been triggered.
>
> 8. I've checked the contents of outgoing emails - this is an 
> accountants practice - the email content is standard, there is nothing 
> there which should trigger bayesian filters.
>
> 9. I've sent emails to other servers under my control running SA - the 
> scores come out perfect at the receiving end.
>
> 10. The emails we send are operational and notices emails to customers 
> - who need them. They call on the phone and complain they haven't 
> received them - just to discover they were sent, but ended up in the 
> junk.
>
> 11. Emails we send to any other domains are never a problem spam-wise.
>
> I can't really think of anything else to try - have I missed anything? 
> Are Hotmail/Outlook.com spam filters a complete lottery?


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    <font face="Arial">Microsoft use their own methods of detection
      including based on reputation and 'length of service' - ie, if you
      have only just started sending emails out from your own address
      (which you have) then they may well consider you suspicious.
      Theres not much yo can do about it.   More info here:
      <a class="moz-txt-link-freetext" href="https://mail.live.com/mail/troubleshooting.aspx">https://mail.live.com/mail/troubleshooting.aspx</a><br>
      <br>
      <br>
    </font><br>
    <div class="moz-cite-prefix">On 19/09/2017 07:25, Sebastian Arcus
      wrote:<br>
    </div>
    <blockquote
      cite="mid:e0e87cbc-23ff-6af8-967c-8a72150be675@open-t.co.uk"
      type="cite">This is a bit off topic as it is not directly related
      to SA, but I'm hoping that with the email and spam expertise on
      this group, someone might throw in a useful idea - which would be
      much appreciated.
      <br>
      <br>
      I have this problem on one site where most emails we send to
      Hotmail/Outlook.com/Live.com email addresses end up in Junk at the
      recipient's end. Things I have tried:
      <br>
      <br>
      1. I've setup SPF, DKIM, DMARC (and set it to 'reject').
      <br>
      <br>
      2. We used to smart relay outbound email through the hosting
      provider (1and1), but now changed to send directly from our own IP
      address, so that we can control the reputation of the sending IP -
      no change.
      <br>
      <br>
      3. I've checked our public IP and the domain name at mxtoolbox.com
      - all tests pass (the public IP has been delisted from the
      Spamhaus non-MX/end-user IP database).
      <br>
      <br>
      4. I've setup forward and reverse DNS entries for our IP address.
      <br>
      <br>
      5. I've checked with all DNS blocklists/blacklists I could find -
      our domain or IP address is not flagged up anywhere.
      <br>
      <br>
      6. This is a small network which I've been managing for years -
      the domain name has not been used to send marketing/lists email of
      any sort - so the historic reputation should be fine.
      <br>
      <br>
      7. I've setup a monitor and block on port 25 outbound on the
      network firewall - in case there is a trojan on a machine on the
      network sending out spam and ruining the reputation of our IP -
      it's never been triggered.
      <br>
      <br>
      8. I've checked the contents of outgoing emails - this is an
      accountants practice - the email content is standard, there is
      nothing there which should trigger bayesian filters.
      <br>
      <br>
      9. I've sent emails to other servers under my control running SA -
      the scores come out perfect at the receiving end.
      <br>
      <br>
      10. The emails we send are operational and notices emails to
      customers - who need them. They call on the phone and complain
      they haven't received them - just to discover they were sent, but
      ended up in the junk.
      <br>
      <br>
      11. Emails we send to any other domains are never a problem
      spam-wise.
      <br>
      <br>
      I can't really think of anything else to try - have I missed
      anything? Are Hotmail/Outlook.com spam filters a complete lottery?
      <br>
    </blockquote>
    <br>
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