How to set up the Health Report Outlook Mailer
Posted by Mike 
Last updated: May 7, 2025 
Microsoft’s Health Report add-in for Windows Server Essentials only allows the use of SMTP servers that support Basic authentication (i.e., authentication via a username and password) when enabling the sending of Health Report emails. However, since Microsoft no longer supports the use of Basic authentication with their Microsoft 365 and Outlook.com email services, you cannot use Windows Server Essentials to send health report emails from those account types now (i.e., from Microsoft personal, or organizational, accounts with email addresses ending in @outlook.com, @live.com, @hotmail.com, @msn.com, and Microsoft 365 email addresses).
The Health Report Outlook Mailer bypasses this limitation by extending the built-in health report emailing feature of Windows Server Essentials, thereby allowing you to use Modern (token-based) authentication to securely send emails from your Microsoft 365 / Outlook.com account.
INFO: The Health Report Outlook Mailer is made available as part of the WSEE Installer Version 10.0.14393.7876 (Revision 3) or greater.
This tutorial will show you all the steps needed to set up the Health Report Outlook Mailer so that you can start sending health reports from Windows Server Essentials using your Microsoft account.