Send Test Email Results in failed : 503 5.5.2 Send hello first

SYSTEM INFORMATION
OS type and version Ubuntu 20.04.4
Webmin version 1.994

Hello,
I am trying to set up notification via Webmin->Webmin Configuration->Sending Emails.

SMTP Remote mail server: smtp-mail.outlook.com
Port: 587
USE SMTP Encryption: STARTTLS
Login as: username and password
SMTP authentication method: Login

When Sending test message I get the error:

… sending failed : SMTP command mail from: webmin@azure-webserver01.domain.com failed : 503 5.5.2 Send hello first [BL0PR02CA0056.namprd02.prod.outlook.com]

Is your SSL properly configured for mail? I think Exchange rejects AUTH on unsecured connections, including self-signed or unrecognized certs.

You can test it at

https://www.immuniweb.com/ssl/

Richard

I bet that is it! I have to re create the VM so I will test that as soon as I get it set back up.

Thank you, @RJM_Web_Design

1 Like

My pleasure.

Richard