Sending Email using Office 365

If after configuring your SimpleHelp server to use Office 365 as your email provider (SMTP server) you find that it does not work as expected you may either have an incorrect configuration or the problem may be that you need to set up an SMTP relay in order to use your Office 365 subscription in this way:

https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/how-to-set-up-a-multifunction-device-or-application-to-send-email-using-office-3

You may also need to set up an app-specific password to give your SimpleHelp server permission to log in without using OAuth.