AUTHENTICATE failed. Service desk, custom email with office 365

[grant-transition]

Hi,

I am trying to implement the 'Custom email address' on Service Desk. I have an office 365 account and created an alias. I have tested this is working which it is. I have also doubled checked my password by logging out of my account, and logging back in. So I'm certain these two aspects are correct.

Office suggests my Imap setting should be as follows:

Server name: outlook.office365.com
Port: 993
Encryption method: TLS 

I have entered these into the form provided under 'Add a custom email address' and receive the following error.

Error: Unfortunately JIRA couldn't connect to the mail server. Here is what the mail server said: "AUTHENTICATE failed." Check out our troubleshooting docs for help resolving the issue.

Help appreciated

[Andy Heinzer]

Is this Jira Cloud or Jira Server?

From the response you got, it would appear that Jira is getting an authentication failure message back from the mail server.   I would want to know more about the settings here:

For example, can you share with us the email address, username, email protocol?

My thought here is that sometimes if the username does not match the email address referred to the user is unable to login

Ultimately, I would like to see more detailed logs from Jira when this happens to understand why it is happening. If this is server, then there are likely logs we can turn up debugging logging on to learn more. However if this is cloud, perhaps we can create a support request with our Cloud support team to see if perhaps they can pull logs from this environment to better understand why we are seeing this particular authentication error.