We are using the free ipMonitor tool to monitor pings on all production servers. I have all of the settings in place for Office 365 email notifications but they fail to get to the accounts. They work when I point them to a gmail.com or outlook.com account but Office 365 accounts fail.
SMTP: smtp.office365.com
Port: 587
tls is active
encryption is turned on in the credentials settings and allowed over SSL