Trying to configure Outgoing Mail using Office365 SMTP

[kambiz-rahem]

I have all the SMTP settings of Office365 for my outgoing mail configuration, but while trying to test connection I get the message " SocketTimeoutException: connect timed out"

Although with the exactly same settings I was able to get mail notifications automatically. After the JIRA version has been upgraded mail sending has stopped. Any suggestions in regards would be greatly appreciated.

[Nic Brough -Adaptavist-]

"read timed out" means that Jira got no response from the server.  This happens when

• Your network can resolve the mail server name, but may not carry traffic to it (blocked port or route etc)
• The mail server is reachable, but you have the wrong port
• The mail server is not responding for some reason - incorrect credentials will usually get an error message back telling you so, but not always.  The usual reason is that the mail server is not set up to allow mail for the user you've given, or does not have smtp enabled

[Rajesh Ramankutty]

Hi @Nic Brough -Adaptavist- 

i have problem in configuring outgoing mail in jira of office 365 account could you help in this?

[Nic Brough -Adaptavist-]

Possibly.  What is the problem?

[Edwin Kyalangalilwa]

Hi Mohammed,

Can we see a screenshot of your configuration?

Currently I am able to connect using

protocol: SECURE_IMAP
host: outlook.office365.com
port: 993
timeout:10000

Also, check your settings

Office365 SMTP configuration receives authentication errors 

[kambiz-rahem]

Thank you for your reply attached is the screen shot for my outgoing email configuration and the error message. in the timeout space I have tried both 0 and 10000 values.

[siboconnection]

I had this problem with a shared microsoft email account. I was able to solve the problem by resetting the shared user account password, according to the instructions in the comments on https://jira.atlassian.com/browse/JRASERVER-30688

Here are the steps:

1. Open the Microsoft 365 admin center.
2. Go to Users > Active users
3. Click the shared user you created for Jira
4. Click Reset password
5. Follow the instruction to create a new password, then use the new password

[Peter Hamilton-Harding]

You need to use a different hostname for this, e.g. tenant.mail.protection.outlook.com (replace this with the MX endpoint for your O365 tenant, always ends in mail.protection.outlook.com

[Maciek Grischke]

How secure is direct send?

[Nic Brough -Adaptavist-]

No less secure than other methods.