Once Security Awareness training is enabled on your Proofpoint account, this can be set up Safelisting & Advanced Delivery for M365 by completing the following tasks:


Create Mail Flow Rule


In the M365 Exchange Admin Center under Mail Flow > Rules (https://admin.exchange.microsoft.com/#/transportrules), create the following rule:


  • Apply this rule if
    • The sender > IP address is in any of these ranges or exactly matches
      • 107.23.16.222, 54.173.83.138, 107.20.210.250, 52.1.14.157 
  • Do the following
    • Modify the message properties > set the spam confidence level (SCL)
      • -1 or "Bypass spam filtering"
    • Modify the message properties > set a message header
      • Set the message header X-MS-Exchange-Organization-SkipSafeLinksProcessing to the value 1


For IP Addressed to be added for safelisting, pick the following depending on the stack:

    North American Training Platform IPS

  • 107.20.210.250
  • 52.1.14.157

    European Training Platform IPS

  • 54.229.2.165
  • 52.30.130.201

    North American Phishing Assessment IPS

  • 107.23.16.222
  • 54.173.83.138

    European Phishing Assessment IPS

  • 52.17.45.98
  • 52.16.190.81


Configuring Advanced Delivery Policy


To prevent Microsoft from erroneously generating informational alerts on Proofpoint's phishing simulation emails, an advanced delivery policy can be implemented in M365. This can be completed through the following steps:




  • Under Domain, add the following:
    • securityeducation.com
  • Under Sending IP, add the following items depending on your region:
    • US: 107.23.16.222 and 54.173.83.138
    • EU: 52.17.45.98 and 52.16.190.81
  • When finished, click Save at the bottom of the page



For more details for Safelisting and Adding domains to Advanced delivery click on the articles below:

Security Awareness Safelisting (US)

Security Awareness Safelisting (EU)