Outgoing SMTP Mail Server Authentication Unsuccessful

Software N3B July 16, 2020

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

 

2 answers

1 accepted

1 vote
Answer accepted
Nic Brough -Adaptavist-
Community Leader
Community Leader
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July 16, 2020

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.

Software N3B July 16, 2020

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.

Nic Brough -Adaptavist-
Community Leader
Community Leader
Community Leaders are connectors, ambassadors, and mentors. On the online community, they serve as thought leaders, product experts, and moderators.
July 16, 2020

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")

Software N3B July 20, 2020

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

0 votes
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