Problem

Jira applications fail to send outbound mail, throwing the below exception in the logs. This occurs even if the system memory has been increased and the SMTP server has been verified as not blocking the Jira applications from sending emails.

The following appears in the atlassian-jira.log:

2011-04-04 16:43:03,841 http-8080-4 ERROR the.hulk 1002x152x1 1wkhzzq 11.22.33.xx,127.0.0.1 /secure/admin/SendBulkMail.jspa [action.admin.mail.SendBulkMail] Error sending e-mail.
com.atlassian.mail.MailException: javax.mail.MessagingException: Exception reading response;
  nested exception is:
    java.net.SocketTimeoutException: Read timed out
    at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:169)
    at com.atlassian.jira.web.action.admin.mail.SendBulkMail.doExecute(SendBulkMail.java:252)
    at webwork.action.ActionSupport.execute(ActionSupport.java:165)

Note that other errors might also be thrown in the Jira logs:

• Example 1

  2016-03-11 09:56:47,557 WARN [] Sending mailitem com.atlassian.support.tools.salext.mail.SupportRequestMailQueueItem@6c57ea6 username 123x4567x8 abcde1 1.2.3.4 /secure/admin/MailQueueAdmin.jspa An error has occurred whilst closing the connection to the outgoing mail server: AA ServiceDesk Out. This could be caused by a time-out on closing this connection, increase the timeout in smtp server configuration. Alternatively, set the 'mail.smtp.quitwait' (or 'mail.smtps.quitwait' for ssl) system property to false.
  javax.mail.MessagingException: Can't send command to SMTP host;
        nested exception is:
          java.net.SocketException: Software caused connection abort: socket write error
      at com.sun.mail.smtp.SMTPTransport.sendCommand(SMTPTransport.java:2163) [mail-1.4.5.jar:1.4.5]
      at com.sun.mail.smtp.SMTPTransport.sendCommand(SMTPTransport.java:2150) [mail-1.4.5.jar:1.4.5]
      at com.sun.mail.smtp.SMTPTransport.close(SMTPTransport.java:1220) [mail-1.4.5.jar:1.4.5]
      at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:183) [atlassian-mail-2.5.6.jar:?]
      at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:150) [atlassian-mail-2.5.6.jar:?]
      at com.atlassian.support.tools.salext.mail.AbstractSupportMailQueueItem.send(AbstractSupportMailQueueItem.java:61) [plugin.2238643682187341319.stp-3.7.22_1457584780532.jar:3.7.22]
      at com.atlassian.support.tools.salext.mail.SupportRequestMailQueueItem.send(SupportRequestMailQueueItem.java:56) [plugin.2238643682187341319.stp-3.7.22_1457584780532.jar:3.7.22]
  ...

• Example 2

  2016-03-11 09:56:47,557 ERROR [] Sending mailitem com.atlassian.support.tools.salext.mail.SupportRequestMailQueueItem@6c57ea6 username 123x4567x8 abcde1 1.2.3.4 /secure/admin/MailQueueAdmin.jspa Error occurred in sending e-mail: com.atlassian.support.tools.salext.mail.SupportRequestMailQueueItem@6c57ea6
  com.atlassian.mail.MailException: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM
  
  at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:213) [atlassian-mail-2.5.6.jar:?]
  at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:150) [atlassian-mail-2.5.6.jar:?]
  at com.atlassian.support.tools.salext.mail.AbstractSupportMailQueueItem.send(AbstractSupportMailQueueItem.java:61) [?:?]
  at com.atlassian.support.tools.salext.mail.SupportRequestMailQueueItem.send(SupportRequestMailQueueItem.java:56) [?:?]
  at com.atlassian.mail.queue.MailQueueImpl.sendBuffer(MailQueueImpl.java:66) [atlassian-mail-2.5.6.jar:?]
  at com.atlassian.jira.mail.JiraMailQueue$1.apply(JiraMailQueue.java:51) [JiraMailQueue$1.class:?]
  at com.atlassian.jira.mail.JiraMailQueue$1.apply(JiraMailQueue.java:48) [JiraMailQueue$1.class:?]
  at com.atlassian.jira.util.velocity.DefaultVelocityRequestContextFactory.runWithStaticBaseUrl(DefaultVelocityRequestContextFactory.java:110) [DefaultVelocityRequestContextFactory.class:?]
  at com.atlassian.jira.util.DefaultBaseUrl.runWithStaticBaseUrl(DefaultBaseUrl.java:50) [DefaultBaseUrl.class:?]
  ...
  

Environment

Jira Server/Data Center on any version from 8.0.0.

Cause

This is known to be caused by either of the following:

• The network cannot transfer the data to the mail server within the specified time interval in the mail server timeout (this can subsequently cause Jira to exhibit the bug JRASERVER-67825 - Getting issue details... STATUS )
• Exchange servers have Message Throttling - Jira applications will send outbound mail dependent upon the mail configuration, which is by default every minute. At this point a significant number of queued mails may be sent within a short period of time, causing throttling to engage.
• Inbound rules in the network security group (Network Network Deny) on the application is blocking the incoming mail server acknowledgment message after Jira initiates the connection to the mail server. 

Resolution

• Increase the timeout value for the mailbox(s) affected as in our Configuring an SMTP mail server to send notifications documentation. Increasing the value in increments of 10000 (10 seconds) is suggested until the errors are resolved. We also recommend contacting the network administrator to isolate any causes of network traffic slowness. For example, an Anti-virus application scanning all outbound traffic may contribute to this behavior.

java.net.SocketTimeoutException: connect timed out
 
DEBUG SMTP: trying to connect to host "email-smtp.us-east-1.amazonaws.com", port 465, isSSL true
220 email-smtp.amazonaws.com ESMTP SimpleEmailService-1062777087 BbfCtWdIGnSiqZ8zpXzm
DEBUG SMTP: connected to host "email-smtp.us-east-1.amazonaws.com", port: 465
EHLO 12.34.65.78
421 Timeout waiting for data from client.

• Remove the rule and the emails should be flushed out of the queue.