Summary

When using Automation For Jira, it is possible to configure a rule that will automatically send emails to a list of users by adding to the recipient list:

• a user picker field (Reporter, Assignee, Custom Field...)
• a group picker field
• a group
• specific email addresses
• the user who initiated the rule

The purpose of this article is to list the most common scenarios where the rule might fail to send the email to some or all the users as per the the rule configuration.

Environment

• Jira Server/Data Center on any version from 8.0.0
• Automation For Jira (A4J) on any version

Note about the "Send Email" action

Something that is very important to note about the Send Email action is that it works differently than the regular Jira notification feature. The table below lists the main differences between both mail features.

Diagnosis

To troubleshoot this type of issue and to identify which root cause might be relevant, please follow the steps below:

• Go to the page ⚙ > System > Logging and Profiling
  • Click on Enable on outgoing mail logging
  • Then underneath that click Enable Debugging
• Replicate the issue by triggering the rule that is sending the email
• Check the the Jira outgoing mail logs in the file <JIRA_HOME>/log/atlassian-jira-outgoing-mail.log
  • Look for entries that contain the string "Sending mailitem To=" along with "Subject=<SUBJECT_FROM_ACTION>" (<SUBJECT_FROM_ACTION> being the subject configured in the "Send Email" action)

    • For example:

      2024-11-26 14:43:25,700+0000 DEBUG [] Sending mailitem To='someaddress2@atlassian.com,someaddress@atlassian.com,someaddress3@atlassian.com' Subject='Test from A4J' From='jiraoutgoingmailserver@gmail.com' FromName='' Cc='' Bcc='' ReplyTo='' InReplyTo='null' MimeType='text/plain' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@1f56bfe9' MessageId='null' ExcludeSubjectPrefix=true' admin 883x2771x1 yh1nw2 172.29.211.209,172.50.0.3 /secure/admin/MailQueueAdmin.jspa [c.atlassian.mail.outgoing] Message was sent with Message-Id <465617458.15.1732632205200@d7a7a59de671>

  • If you see the error "Invalid Addresses" in the logs, similar to one shown below, then Root Cause 1 is relevant:

    2024-11-26 14:34:00,899+0000 ERROR [] Sending mailitem To='héy@gmail.com,anotheruser@gmail.com,someuser@gmail.com' Subject='Test from A4J' From='jiraoutgoingmailserver@gmail.com' FromName='' Cc='' Bcc='' ReplyTo='' InReplyTo='null' MimeType='text/plain' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@75ee25b6' MessageId='null' ExcludeSubjectPrefix=true' anonymous    Mail Queue Service [c.a.mail.queue.MailQueueImpl] Error occurred in sending e-mail: To='héy@gmail.com,anotheruser@gmail.com,someuser@gmail.com' Subject='Test from A4J' From='jiraoutgoingmailserver@gmail.com' FromName='' Cc='' Bcc='' ReplyTo='' InReplyTo='null' MimeType='text/plain' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@75ee25b6' MessageId='null' ExcludeSubjectPrefix=true'
    com.atlassian.mail.MailException: javax.mail.SendFailedException: Invalid Addresses;
          nested exception is:
        	com.sun.mail.smtp.SMTPAddressFailedException: 555-5.5.2 Syntax error, cannot decode response. For more information, go to
        555-5.5.2  https://support.google.com/a/answer/3221692 and review RFC 5321
        555 5.5.2 specifications. ffacd0b85a97d-3825fd04ec7sm13503049f8f.110 - gsmtp
        
    	at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:240) [atlassian-mail-6.0.2.jar:?]
    	at com.atlassian.mail.queue.SingleMailQueueItem.send(SingleMailQueueItem.java:39) [atlassian-mail-6.0.2.jar:?]
    	at com.atlassian.jira.mail.CountingMailQueueItemWrapper.send(CountingMailQueueItemWrapper.java:26) [classes/:?]
    	at com.atlassian.mail.queue.MailQueueImpl.sendBufferUnderLock(MailQueueImpl.java:83) [atlassian-mail-6.0.2.jar:?]
    	at com.atlassian.mail.queue.MailQueueImpl.sendBuffer(MailQueueImpl.java:47) [atlassian-mail-6.0.2.jar:?]
    
    

  • If you don't see any error, move on to the next steps below
  • Check the header that contains the list of recipients configured in the automation rule (To=, Cc= or Bcc= depending on the rule configuration)
    • If you see that the list of recipient contains exactly 100 email addresses, and if the rule was configured to send an email to a group of more than 100 users, then Root Cause 2 is relevant
    • If the list of recipients does not contain exactly 100 email addresses, then Root Cause 3 "might" be relevant

Cause

Root Cause 1 - At least one of the recipient of the email has an invalid address

If at least one of the recipient of the email has an invalid address (for example héy@gmail.com, which contains the invalid character é), the rule will fail to send the email to all the recipients, even if the other recipients have a correct address. The reason why other recipients will not receive the email is because the Send Email action will send 1 single email with all the user email addresses in the recipient list (instead of sending 1 separate email to each recipient). If at least 1 address is invalid, the SMTP Mail Server will reject the email.

Root Cause 2 - The "Send Email" action can only send emails to 100 users max

The Send Email action can only send an email to the first 100 users of a Jira group. If a group contains more than 100 users, any user located after the 100th user will not receive the email. 

There is an open feature request meant to change this behavior: JIRAAUTOSERVER-859 - Getting issue details... STATUS

Root Cause 3 - The SMTP Mail Server is configured with a recipient limit

Some mail server such as Exchange servers can be configured with a recipient limit, as described in this Microsoft Documentation about Recipient limits. As mentioned in this documentation, Exchange Servers have a setting called Maximum number of recipients in a message that's sent by the specific sender which is unlimited by default, but which can be changed to a specific value.

Since the Send Email action will send 1 single email with all the user email addresses in the recipient list, if the Mail Server is configured with a recipient limit, it is possible that the rule will either completely fail, or will only be able to send the email to a limited number of users, depending on how the SMTP Mail Server handles this limit.

Solution

Solution for Root Cause 1

• Identify the invalid email address(es) in the error from outgoing mail logs (look for invalid email characters, such as è, ë, é, ä, etc...)
• Go to Jira's user management page in ⚙ > User Management > Users 
• Search for the invalid email address to identify the user this address belongs to, and fix it
  
  • Note that, if the user was synced from an external LDAP directory, you might have to fix the email address in the LDAP directory first and then sync Jira with this directory

Solution for Root Cause 2

Due to the feature limitation, there is no straight forward solution to it.

One possible solution consists in:

• Splitting the group into 2 smaller groups of 100 users max
• Splitting the Send Email action into 2 separate Send Email actions, and configuring each of them with a different group

Solution for Root Cause 3

For this solution, we recommend reaching out to your Mail Server administrator to ask then to increase the recipient limit.