Client was not authenticated to send anonymous mail during MAIL FROM

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Support_Josh

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Joined: Thu Feb 16, 2017 11:20 am

Post by Support_Josh » Fri Feb 15, 2019 2:59 pm
Question:
Why is the error "Client was not authenticated to send anonymous mail during MAIL FROM" message appearing in my goanywhere.log when trying to send Success/Failure emails from a scheduler or when a system notification attempts to send? We have a resource connecting to the same SMTP server that is configured in the Global Settings > SMTP Settings page but only the scheduler emails are failing to be sent.

Here is the entire log entry:
11/7/17 3:40:17 PM 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...

Answer:
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.

For more information when using this type of configuration, please refer to this Microsoft article: https://support.office.com/en-us/articl ... US#option2
Joshua Przybysz
Senior Support Analyst
e. goanywhere.support@helpsystems.com
p. 1.800.949.4696
w. HelpSystems.com
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