How to configure outgoing mail SMTP setting using Office365

[Balamurugan S]

After Configure SMTP setting of Office365 for outgoing mails in Jira, I'm getting Socket timeout and test mail failed 

[Aditya Verma]

Hi @Balamurugan S ,

Can you check if you are using correct port and protocol. You can also try increasing the timeout in multiples of 10000 and see if the issue gets resolved.

Thanks,
Aditya

[Balamurugan S]

Hi @Aditya Verma 

Below is my Configuration. and i got below error msgs, attached screenshot for your reference. 

[Aditya Verma]

Can you help me with your Jira version, some options look different to me in screenshot.
Simultaneously, you can check your Office365 account by logging in directly with Microsoft to make sure that a password change is not currently mandated. Since Microsoft frequently requires password change.

Thanks,
Aditya

[Balamurugan S]

Jira version 9.6

i can login Microsoft using Authenticator app or OTP

[Aditya Verma]

It means you have two factor authentication enabled for your account. In this case you would need to create a separate application password for using it with Jira. I'll quote the Atlassian Team from this community discussion.

"When 2FA is enabled for Office 365, you'll need to issue an app password for Jira to connect to the mailbox. This is a separate password from what you'd use for the account, and allows Jira (or another application) to bypass 2FA. You enter this in the standard password field in the application (and you don't enter the normal account password anymore).

The Microsoft documentation for using app passwords is available here - and although it's at the top of the document, I want to call out here as well that app passwords need to be enabled for your organization by an Azure/Office365 admin, or you won't see the options mentioned in the rest of the documentation that allow you to create a new one."

Thanks,

Aditya