Symptoms

When attempting to send a test mail through a JIRA application, it fails with a "530 5.7.1 Client was not authenticated" error.

The following appears in the atlassian-jira.log:

2012-09-05 16:32:43,193 http-8280-5 ERROR u18547 992x517290x1 gqc9dj 10.7.105.153 /secure/admin/SendBulkMail.jspa [action.admin.mail.SendBulkMail] Error sending e-mail.
com.atlassian.mail.MailException: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.1 Client was not authenticated
	at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:183)
	at com.atlassian.jira.web.action.admin.mail.SendBulkMail.doExecute(SendBulkMail.java:252)
	at webwork.action.ActionSupport.execute(ActionSupport.java:165)
	at com.atlassian.jira.action.JiraActionSupport.execute(JiraActionSupport.java:76)
	at webwork.interceptor.DefaultInterceptorChain.proceed(DefaultInterceptorChain.java:39)
	at webwork.interceptor.NestedInterceptorChain.proceed(NestedInterceptorChain.java:31)
	at webwork.interceptor.ChainedInterceptor.intercept(ChainedInterceptor.java:16)
	at webwork.interceptor.DefaultInterceptorChain.proceed(DefaultInterceptorChain.java:35)
	at webwork.dispatcher.GenericDispatcher.executeAction(GenericDispatcher.java:205)
	at webwork.dispatcher.GenericDispatcher.executeAction(GenericDispatcher.java:143)
	at com.atlassian.jira.web.dispatcher.JiraWebworkActionDispatcher.service(JiraWebworkActionDispatcher.java:152)
	at javax.servlet.http.HttpServlet.service(HttpServlet.java:717)
	...
Caused by: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.1 Client was not authenticated
	at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2057)
	at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1580)
	at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1097)
	at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:156)
	...

OR

com.atlassian.mail.MailException: com.sun.mail.smtp.SMTPSendFailedException: 530 Authentication required
at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:193)
at com.atlassian.jira.plugins.mail.webwork.SendTestMail.doExecute(SendTestMail.java:107)
at webwork.action.ActionSupport.execute(ActionSupport.java:165)
at com.atlassian.jira.action.JiraActionSupport.execute(JiraActionSupport.java:82)
at webwork.interceptor.DefaultInterceptorChain.proceed(DefaultInterceptorChain.java:39)
at webwork.interceptor.NestedInterceptorChain.proceed(NestedInterceptorChain.java:31)
at webwork.interceptor.ChainedInterceptor.intercept(ChainedInterceptor.java:16)

Cause

• This error is generated by the SMTP server when it requires authentication, and credentials have not been entered into the configuration of the JIRA application.
• Firewall blocked the authentication, or there is a third-party application monitoring SMTP traffic.
  • Firewall may filter out/ replace the SMTP traffic or the SMTP commands.

  • Results of Telnet:

    [root@km ~]# telnet <hostname> 25
    Trying <ip address>....
    Connected to <hostname>.
    Escape character is '^]'.
    220 *****************************************************************************************************************
    EHLO <hostname>
    500 Syntax error, command "XXXX <hostname>" unrecognized
    HELO <hostname>
    250 <hostname> Hello <hostname> ([IP ADDRESS]), pleased to meet you
    AUTH LOGIN ERTYUiopolJHGFDGhjkLOIUYTFDvbnASDasdsaM== fASIafqYU
    500 Syntax error, command "XXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXXX" unrecognized

  • Firewall or a third-party application replaced the character to string "XXXXXXXXX"
  • This results to Javamail thinking that the server does not support the extended set of command, and does not issue the AUTH LOGIN command to authenticate.

    • the failing of the EHLO command causes the Javamail to not get this information:

      250-HELP
      250-AUTH LOGIN
      250-SIZE
      250 PIPELINING

Resolution

• Set up the SMTP server as in Configuring JIRA's SMTP mail server to send notifications, ensuring that the correct Username and Password parameters have been entered.

  • You can telnet manually to check on the authentication of Username and Password.
    
    

    telnet <hostname> 25
    220 forchheim160a.linux.rz.db.de ESMTP Service (Lotus Domino Release 8.5.2FP3) ready at Mon, 3 Dec 2012 09:30:45 +0100
    EHLO <hostname> Hello <hostname> ([ip address]), pleased to meet you
    250-HELP
    250-AUTH LOGIN
    250-SIZE
    250 PIPELINING
    HELO <hostname>
    250 <hostname> Hello <hostname> ([IP ADDRESS]), pleased to meet you
    AUTH LOGIN ERTYUiopolJHGFDGhjkLOIUYTFDvbnM== fASIafqYU
    <cut>=235 Authentication successful

• Make sure the Firewall is turned off (or reconfigured to receive command from JIRA server) and there is no third-party application monitoring the SMTP traffic.
  • Telnet from JIRA server to SMTP server
  • Make sure the SMTP server reacts the command sent like EHLO.