title: How to beat Hotmail/Live/Outlook and AOL spam filters? (custom dedicated mail server)
body: <p>I am trying to set up a mail server for my client's web app.</p>
  
  <p>The CentOS/Postfix-based mail server runs on a dedicated VPS from DigitalCocean.</p>
  
  <p>SPF record: check
  DKIM (openDKIM): check
  Clean dedicated IP: check
  Clean domain: check</p>
  
  <p>GMail, Yahoo, Zoho Mail, GMX/mail.com, Yandex Mail - absolutely no problems, all emails get delivered to the Inbox.</p>
  
  <p>However it goes to Junk when sending to AOL and Live/Outlook/Hotmail users. I tried all types of content: plain text emails with a few words, HTML-rich emails and everything in between. The issue seems to be not related to the email content.</p>
  
  <p>Microsoft support does not help much since they basically our server seems to fine and there is something they don't know to trigger their SmartScreen security.</p>
  
  <p>Any thoughts ?</p>