Cannot get outlook integration working

sspinn

Integration with outlook is not working and the debug messages aren't useful.

Host: outlook.office365.com
Security: TLS (unable to test without due to outlook restrictions)
Debug Enabled:

Error

Unable to send email via JavaMail

Prime Messaging Exception
Cause: MessagingException: Exception reading response

Any options to get more verbose logging?

sspinn

Looks like SMTP Auth will never be a usable option with Outlook since the steps to configure it require disabling security defaults on an organisation wide basis: https://learn.microsoft.com/en-us/exchange/clients-and-mobile-in-exchange-online/authenticated-client-smtp-submission

I solved it by using another email broker and leaving Outlook untouched.

paulp

@sspinn Did you figure it out with outlook.office365.com?

SMTP credentials are confirmed valid and working using SWAKS.
We use a GMAIL SMTP too on other tenants which works fine using TLS.

Debug logs: