Create
cancel
Showing results for 
Search instead for 
Did you mean: 
Sign up Log in

It's not the same without you

Join the community to find out what other Atlassian users are discussing, debating and creating.

Atlassian Community Hero Image Collage

Outgoing SMTP Mail Server Authentication Unsuccessful

Edited

We're having issues setting up an outgoing SMTP mail server. The account being used is repeatedly and almost immediately locked when testing connections and sending test emails. We've confirmed hosts, ports, usernames, passwords, different accounts, etc. However, the credentials seem to somehow be sending incorrectly and locking the account, thus failing. Sample log from Send Test Email function below. 

An error has occurred with sending the test email:
com.atlassian.mail.MailException: javax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful

...


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, host=*******, user=jira, password=<null>
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "*******", port 25, isSSL false
220 n3b-mail-01.em-la.doe.gov Microsoft ESMTP MAIL Service ready at Thu, 16 Jul 2020 06:35:45 -0600
DEBUG SMTP: connected to host "*******", port: 25

EHLO *******
250-******* Hello [172.30.0.82]
250-SIZE 37748736
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-AUTH NTLM
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250 XRDST
DEBUG SMTP: Found extension "SIZE", arg "37748736"
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "DSN", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "X-ANONYMOUSTLS", arg ""
DEBUG SMTP: Found extension "AUTH", arg "NTLM"
DEBUG SMTP: Found extension "X-EXPS", arg "GSSAPI NTLM"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "BINARYMIME", arg ""
DEBUG SMTP: Found extension "CHUNKING", arg ""
DEBUG SMTP: Found extension "XRDST", arg ""
DEBUG SMTP: protocolConnect login, host=*******, user=*******, password=<non-null>
DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM XOAUTH2
DEBUG SMTP: mechanism LOGIN not supported by server
DEBUG SMTP: mechanism PLAIN not supported by server
DEBUG SMTP: mechanism DIGEST-MD5 not supported by server
DEBUG SMTP: Using mechanism NTLM
DEBUG NTLM: type 1 message: 4E 54 4C 4D 53 53 50 00 01 00 00 00 03 A2 00 00 00 00 00 00 30 00 00 00 10 00 10 00 20 00 00 00 6E 33 62 2D 6A 69 72 61 2D 63 6F 72 65 2D 30 31
DEBUG SMTP: AUTH NTLM command trace suppressed
DEBUG NTLM: type 3 message: 4E 54 4C 4D 53 53 50 00 03 00 00 00 18 00 18 00 94 00 00 00 18 00 18 00 AC 00 00 00 00 00 00 00 40 00 00 00 34 00 34 00 40 00 00 00 20 00 20 00 74 00 00 00 00 00 00 00 C4 00 00 00 01 82 00 00 6E 00 33 00 62 00 69 00 74 00 73 00 75 00 70 00 70 00 6F 00 72 00 74 00 40 00 65 00 6D 00 2D 00 6C 00 61 00 2E 00 64 00 6F 00 65 00 2E 00 67 00 6F 00 76 00 6E 00 33 00 62 00 2D 00 6A 00 69 00 72 00 61 00 2D 00 63 00 6F 00 72 00 65 00 2D 00 30 00 31 00 E9 69 33 46 CD 86 E9 6A A8 47 2F 81 BA 25 63 88 1A A6 8C F9 22 EB 68 B7 15 42 64 41 85 1D 3B 20 CD 63 0A 79 B9 4B C9 E1 6D B3 F1 30 7B 1A F5 6C
DEBUG SMTP: AUTH NTLM failed

 

1 answer

1 accepted

0 votes
Answer accepted

I'm afraid you have got as far as you can debugging it from the Jira side.

Your mail server is rejecting the connection.  You'll need to question the mail server to see why.

Except that every time an account is used to authenticate for that mailbox, whether it’s the service account itself or my personal account with privileges to the mailbox, that account gets locked out in Active Directory. If the Exchange servers were rejecting the connection the authentication shouldn’t get that far. I still think Jira is passing creds wrong.

You'll need to ask the mail server about that.

It's unlikely that Jira is "passing it wrong", as no-one has logged anything I can find that suggests they've found it doing it wrong in 8.x (well, there are a few, but they've all been resolved with "mail server mis configured, not Jira")

We created an SMTP Receive Connector specifically for Jira and it fixed it. Thanks for the guidance. 

Suggest an answer

Log in or Sign up to answer
DEPLOYMENT TYPE
SERVER
VERSION
8.4.2
TAGS

Community Events

Connect with like-minded Atlassian users at free events near you!

Find an event

Connect with like-minded Atlassian users at free events near you!

Unfortunately there are no Community Events near you at the moment.

Host an event

You're one step closer to meeting fellow Atlassian users at your local event. Learn more about Community Events

Events near you