Scheduled SmartEvent Reports to O365 fail - smtp.office365.com

[Danny]

We are experiencing an issue with the "Test Server Connectivity" function in R81.10 JHF 55 for scheduled SmartEvent reports.
The function works for all Non-O365 SMTP servers as shown below:

For Office365 the following error is shown:

We tried every possible combination to no avail.

At the CLI a SMTP connection is possible:

$RTDIR/log/smartview.log shows:

ERROR   [TaskExecutor Worker 4] (EmailSender.java:77) - Error sending email message.
properties : {mail.smtp.starttls.enable=true, mail.smtp.port=587, mail.smtp.auth=true, mail.smtp.host=smtp.office365.com}
EmailOptions : [from : **********], [properties : {}], [encryption : TLS], [host : smtp.office365.com], [port : 587]

javax.mail.AuthenticationFailedException: 421 4.7.66 TLS 1.0 and 1.1 are not supported. Please upgrade/update your client to support TLS 1.2. Visit https://aka.ms/smtp_auth_tls. [BE1P281CA0036.DEUP281.PROD.OUTLOOK.COM]

sk178125 and sk179628 look similar. However, their -Solution- doesn't really help us further.

We opened a SR several weeks ago, provided CPinfo, double checked authentication and encryption settings. No help yet.

Did anyone else run into the same issue and knows a working solution?

[Alex-]

MS requires TLS on port 587 with authentication.

[Danny]

Of course. I wrote "We tried every possible combination to no avail" which includes TLS (port 587).

[KennyManrique]

Hi Danny.

A few days ago, for authenticated mail I had to change from port 25 to port 587 for O365 DynamicID to work.

For unauthenticated mail you should follow option 2 of official ms doc

[Danny]

This doesn't help in my case. I tried None, SSL, TLS with port 587:

[KennyManrique]

Did you try option 2 of the link?

For non auth scenarios you should point to a different address than smtp.office365.com (i.e. yourcompany.mail.protection.outlook.com) and use port 25.