Client was not authenticated to send anonymous mail during MAIL FROM

[Support_Josh]

Overview
The error message “Client was not authenticated to send anonymous mail during MAIL FROM” appears in the goanywhere.log when Success/Failure emails are sent from a scheduler or when a system notification attempts to send. Although a resource is configured to connect to the same SMTP server specified in Global Settings > SMTP Settings, only the scheduler emails fail to send.
Log entry:
ERROR Failed to send email notification for the scheduled job 'email schedule test'.
com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [*.prod.outlook.com]...Stack trace omitted...

Environment
GoAnywhere MFT - all versions

Implementation
When using Office 365 as a mail relay, the SMTP resource and the Global Settings > SMTP Settings connect to the relay server differently and require different parameters. Even if the test on the Global SMTP Settings page works, it may not work when a Scheduler uses those settings.
To fix this, use the MX endpoint for the Office 365 account that is being used on the Global SMTP in the Host field setting and use port 25 to connect to that host. TLS/SSL is also supported with port 25 in this configuration according to Microsoft. That will allow outbound messages from GoAnywhere MFT when trying to send when using the Scheduler.