In order to send outgoing emails from Service Desk Manager using Office 365 Mail, please follow these steps:
Log in to the Office365 website (outlook.office365.com) using the credentials for the account that you wish to use with outgoing mail. Please note the web site you need to open is not the top page of the office365. It is necessary to open the top page of the Outlook in the Office365 website.
Save the root certificate from the post-login page as a base 64 encoded .cer file, and copy it to the primary server (see steps below)
Populate the following settings in the Administration tab under Options Manager -> Email:
***NOTE: mail_smtp_domain_name may be smtp.office365.com in some instances***
Steps to save the root certificate:
Run your web browser as an Administrator user
Click on the lock in the address bar when you are on the page you wish to save the certificate from
Navigate to the Certification Path tab, click on the root certificate, and click View Certificate
Click on the Details tab, click Copy to File, and choose Base 64 Encoded x.509 (.CER) as the format
Configure the option "mail_ca_cert_path" to point to the local certificate file copied per the above step.
Specific SMTP and IMAP server configuration settings for Office 365 and other online mail products are available to review here: