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
