SMTP Auth Failing as Anonymous

Hi there, 

Trying to config Jira to send SMTP via O365 (Exchange) - Can verify that the connection to the server is successful, but when Jira tries to send test mail, it's being rejected by the server, because it says Jira's trying to send anonymous: 

DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: need username and password for authentication
DEBUG SMTP: protocolConnect returning false,, user=jira, password=<null>
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "", port 587, isSSL false
220 Microsoft ESMTP MAIL Service ready at Fri, 19 Jan 2018 05:52:01 +0000
DEBUG SMTP: connected to host "", port: 587

its showing user=jira, password as <null> - which is NOT what's setup in the SMTP config.

Notification schema is set to default, which is suppose to take the creds entered in the SMTP setup dialogue. doesn't seem to be happening. 

I've tested the correct account with O365 and it seems to be working fine. 
Could use a little help. :-)


1 answer

Hi John,

From the following based on what you have posted here:

DEBUG SMTP: protocolConnect returning false,, user=jira, password=<null>

It seems like the password is null as you have mentioned. Something might have gone wrong with the configuration. What if you just delete the Outgoing Mail configuration on JIRA and reconfigure it again? Do you have the same error?


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