Jira 8.5.3 SMTP Office 365 and STARTTLS

[Gisli Gudmundsson]

Hi, I have Jira software 8.5 and I´m trying to enable SMTP outgoing mail to Office 365. I need to have STARTTLS enabled. I have configured as follows, both with and without the TLS tick. But both do not work, without the tick the authentication is OK but when testing to send mail it comes with an error saying that it requires STARTTLS to work. I have tried to search and I have not found anything that might help. Does anyone know how I can fix this?

[Simon Tost _TNG_]

There is a KB article about this: There is a environment switch

-Dmail.smtp.starttls.enable=true

that can be set to enable / enforce STARTTLS.

Sadly it is mentioned here only for the imap protocol...

(It is also mentioned as an option for the JNDI way of setting up the SMTP connection tough it's not really obvious that this would be transferrable...)

(Not quite related, but: In wilder cases, I suspect the general Java Mail API docu might come in handy. eg. in our case I found the `-Dmail.smtp.userset` very well worth trying, bc. it only gives a very generic 'Problem with username and password' error which does not really help. (Microsoft High Volume Email (HVE) does not seem to implement SMTP NOOP.) To be fair, that setting is also mentioned in the base docu.)