SMTP connection with Office365

Overview:

The legacy SMTP connection is not usable in ReadyWorks when using Office 365. ReadyWorks requires an SMTP relay to authenticate with Office 365 for sending outgoing emails.

This article provides steps to configure an IIS SMTP relay on the ReadyWorks Azure VM to replace the legacy appliance.

Use Case:

For our Customers using Office 365, an authenticated SMTP relay is required to facilitate communication and meet Office 365's security requirements. An IIS SMTP relay running on the ReadyWorks VM provides this authenticated middleman function.

Steps to Configure IIS SMTP Relay:

1. Install the IIS role on your ReadyWorks server (if not already installed)
2. Install the SMTP Server feature
3. In IIS Manager, configure SMTP virtual server
   • Set the IP address to only listen on localhost
   • Select "Outbound only" for the delivery method
   • Set smart host to Office 365 MX address
   • Configure authentication to use Office 365 credentials
4. Next, you'll need to update the ReadyWorks SMTP hostname setting to "localhost"
   • Open up RW Server Task Tray Control Panel
   • Under ‘Services and Modules’, scroll down to PHP 7.x.x -> php.ini
   • Search for the name "SMTP" and update that value to localhost, then save
   • 
5. Restart the ReadyWorks web server to load your updated SMTP hostname
6. Test outbound email connectivity through the new SMTP relay
   • ReadyWorks recommends testing via requesting a password reset email from the login page of ReadyWorks
   • Then verify the email is received successfully
7. If this testing fails, then troubleshoot the IIS relay authentication or make sure you've performed a server reboot to refresh components
8. Once the SMTP relay is working, nest update your firewall rules:
   • Block external SMTP traffic to the server
   • Allow outbound SMTP traffic on port 25
9. Bring the legacy SMTP relay offline for decommissioning or other disposition outside of the communications chain with ReadyWorks