Symptoms

After configuring a Smartform with a rule to send an email using the from address the following error was thrown:

The SMTP server requires a secure connection or the client was not authenticated. The server response was: 5.7.57 SMTP Client was not authenticated to send anonymous mail during MAIL FROM

 

Diagnoses

The 'From Address' item uses the K2Service account ( KUID]@appit.com). This O365 is looking for TLS Credentials and which the account does not have and as such cannot authenticate. This has been logged for fix.
 

Resolution

The user has opted to go with a workaround in which they will create a workflow with an email event and then use 'Start WorkFlow' rule to pass in and the relevant information and then start the workflow thereby sending the desired email.