Unfortunately JIRA couldn't connect to the mail server. Here is what the mail server said: "AUTHENTI

[Lubna Malik]

I am in a bit of a pickle and not sure what's wrong.  We are using a cloud instance of JIRA and have 3 service desk projects successfully using custom email address connected to our O365 mail server. 

I am trying to setup same for a new project, however, receiving below error message: 

"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.

Exchange team is claiming that the new email address has exactly the same settings as the other emails which are successfully working with JIRA and I need to check within JIRA for any issue. I am turning to the community to help troubleshoot this.

[Rami Khader · Accepted solution]

Did you manage to find what was the issue?

Rami

[Lubna Malik]

Yes and No. Our initial email address was bit long we changed it to relatively short one and it connected with Jira. I am not sure if there is any limit on how long an email address can be on Atlassian's end? 

[Nic Brough -Adaptavist-]

Can you try the "send test email" function in the email setup section - that will get you the raw logs of the connection attempt.   Those logs should be enough to tell you what the mail server is saying back to Jira when it tries to connect.  Although I suspect they will just confirm that you've got the wrong username/password combination.

[Lubna Malik]

Thanks, Nick for your reply. Email/Password combination is right because I can log in directly to outlook using the same. 

I am receiving this error while trying to setup the email under email channel menu I believe logs are available for emails when they are already setup? 

[Nic Brough -Adaptavist-]

"Authenticate failed" almost always means the server is running ok, accepting connections, you've connected to it, but either given it a user id that does not exist, or an incorrect password for one that does exist.

Connecting via outlook is not the same as this.

Could you try the test I suggested?  It should give you a full error message, or more detail on the one you've got (some mail servers for example can tell you "authenticate failed" and then more in the log - like "this user exists, but is not allowed to send mail from that address")

[Katie Minks]

I am having the exact same problem and when I send to the email and do SMTP logging, it looks like it goes through as expected.

Your test message has been sent successfully to Digital.Library@company.com

DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: useEhlo true, useAuth false
DEBUG SMTP: trying to connect to host "localhost", port 25, isSSL false
220 ip-10-254-136-181.ec2.internal ESMTP Postfix
DEBUG SMTP: connected to host "localhost", port: 25

EHLO ip-10-254-136-181.ec2.internal
250-ip-10-254-136-181.ec2.internal
250-PIPELINING
250-SIZE 10240000
250-VRFY
250-ETRN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "SIZE", arg "10240000"
DEBUG SMTP: Found extension "VRFY", arg ""
DEBUG SMTP: Found extension "ETRN", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "DSN", arg ""
DEBUG SMTP: use8bit false
MAIL FROM:<jira.servicedesk@company.com>
250 2.1.0 Ok
RCPT TO:<Digital.Library@company.com>
250 2.1.5 Ok
DEBUG SMTP: Verified Addresses
DEBUG SMTP: Digital.Library@company.com
DATA
354 End data with <CR><LF>.<CR><LF>
Date: Thu, 2 May 2019 15:16:58 +0000 (UTC)
From: jira.servicedesk@company.com
To: Digital.Library@company.com
Message-ID: <597872817.24413.1556810218555@ip-10-254-136-181.ec2.internal>
Subject: RE: [JIRA] Test Message From JIRA
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8
Content-Transfer-Encoding: 7bit
X-JIRA-FingerPrint: 43f7fd23d4ea533aba40467126124408
Auto-Submitted: auto-generated
Precedence: bulk

This is a test message from JIRA.
Server: Default SMTP Server
SMTP Port: 25
Description:
From: jira.servicedesk@company.com
Host User Name: null
.
250 2.0.0 Ok: queued as 8775C4393C5
DEBUG SMTP: message successfully delivered to mail server
QUIT