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  1. Jira Cloud
  2. JRACLOUD-60981

Make JIRA more secure to work with Gmail when configuring Outgoing SMTP server

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    Description

      NOTE: This suggestion is for JIRA Cloud. Using JIRA Server? See the corresponding suggestion.

      Summary

      When connecting JIRA to Gmail for Outgoing SMTP Mail, some users might run into the following problem when testing connection

      Unfortunately no connection was possible. Review the errors below and rectify:

      • AuthenticationFailedException: 534-5.7.14 <https://accounts.google.com/signin/continue?sarp=x&xxx=x&xxx=xxxxxxxx
        534-5.7.14 xxxXXxxxXXXXXXXXXxXXXxXxXxXxXxXxXXXxXXXXX_XXxxxXXxXXXxXxXXxxXXxxXXXxxx
        534-5.7.14 xxxXXxx_XXXXXXXXXxXXXxXxXxXxXxXxXXXxXXXXXXXXxxxXXxXXXxXxXXxxXXxxXXXxxx
        534-5.7.14 xxxXXxxxXXXXXXXXXxXXXxXxXxXxXxXxXXXxXXXXXXXXxxxXXxXXXxXxXXxxXXxx-XXxxx
        534-5.7.14 xXX_xxxxXXXXXxXXXxXX-xxxXXXxX> Please log in via your web browser and
        534-5.7.14 then try again.
        534-5.7.14 Learn more at
        534 5.7.14 https://support.google.com/mail/answer/78754 b8sm33119713wjf.9 - gsmtp

      The following is thrown in the logs

      2016-04-05 07:44:00,317 ERROR [] Sending mailitem To='example@email.com' Subject='Your account was created!' From='null' FromName='XXX' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='null' MimeType='text/plain' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@2def3c' MessageId='null' anonymous    Mail Queue Service Error occurred in sending e-mail: To='example@email.com' Subject='Your account was created!' From='null' FromName='XXX' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='null' MimeType='text/plain' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@2def3c' MessageId='null'
      com.atlassian.mail.MailException: javax.mail.AuthenticationFailedException: 534-5.7.14 <https://accounts.google.com/signin/continue?sarp=x&xxx=x&xxx=xxxxxxxx
          534-5.7.14 xxxXXxxxXXXXXXXXXxXXXxXxXxXxXxXxXXXxXXXXX_XXxxxXXxXXXxXxXXxxXXxxXXXxxx
          534-5.7.14 xxxXXxx_XXXXXXXXXxXXXxXxXxXxXxXxXXXxXXXXXXXXxxxXXxXXXxXxXXxxXXxxXXXxxx
          534-5.7.14 xxxXXxxxXXXXXXXXXxXXXxXxXxXxXxXxXXXxXXXXXXXXxxxXXxXXXxXxXXxxXXxx-XXxxx
          534-5.7.14 xXX_xxxxXXXXXxXXXxXX-xxxXXXxX> Please log in via your web browser and
          534-5.7.14 then try again.
          534-5.7.14  Learn more at
          534 5.7.14  https://support.google.com/mail/answer/78754 b8sm33119713wjf.9 - gsmtp
          
      	at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:214) [atlassian-mail-2.5.16.jar:?]
      	at com.atlassian.mail.queue.SingleMailQueueItem.send(SingleMailQueueItem.java:44) [atlassian-mail-2.5.16.jar:?]
      	at com.atlassian.mail.queue.MailQueueImpl.sendBuffer(MailQueueImpl.java:66) [atlassian-mail-2.5.16.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:?]
      	at com.atlassian.jira.mail.JiraMailQueue.sendBuffer(JiraMailQueue.java:48) [JiraMailQueue.class:?]
      	at com.atlassian.jira.service.services.mail.MailQueueService.run(MailQueueService.java:21) [MailQueueService.class:?]
      	at com.atlassian.jira.service.JiraServiceContainerImpl.run(JiraServiceContainerImpl.java:61) [JiraServiceContainerImpl.class:?]
      	at com.atlassian.jira.service.ServiceRunner.runService(ServiceRunner.java:62) [ServiceRunner.class:?]
      	at com.atlassian.jira.service.ServiceRunner.runServiceId(ServiceRunner.java:44) [ServiceRunner.class:?]
      	at com.atlassian.jira.service.ServiceRunner.runJob(ServiceRunner.java:32) [ServiceRunner.class:?]
      	at com.atlassian.scheduler.core.JobLauncher.runJob(JobLauncher.java:153) [atlassian-scheduler-core-1.7.0.jar:?]
      	at com.atlassian.scheduler.core.JobLauncher.launchAndBuildResponse(JobLauncher.java:118) [atlassian-scheduler-core-1.7.0.jar:?]
      	at com.atlassian.scheduler.core.JobLauncher.launch(JobLauncher.java:97) [atlassian-scheduler-core-1.7.0.jar:?]
      	at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.launchJob(CaesiumSchedulerService.java:401) [atlassian-scheduler-caesium-1.3.0.jar:?]
      	at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeLocalJob(CaesiumSchedulerService.java:369) [atlassian-scheduler-caesium-1.3.0.jar:?]
      	at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeQueuedJob(CaesiumSchedulerService.java:347) [atlassian-scheduler-caesium-1.3.0.jar:?]
      	at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService$1.consume(CaesiumSchedulerService.java:255) [atlassian-scheduler-caesium-1.3.0.jar:?]
      	at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService$1.consume(CaesiumSchedulerService.java:252) [atlassian-scheduler-caesium-1.3.0.jar:?]
      	at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeJob(SchedulerQueueWorker.java:65) [atlassian-scheduler-caesium-1.3.0.jar:?]
      	at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeNextJob(SchedulerQueueWorker.java:59) [atlassian-scheduler-caesium-1.3.0.jar:?]
      	at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.run(SchedulerQueueWorker.java:34) [atlassian-scheduler-caesium-1.3.0.jar:?]
      	at java.lang.Thread.run(Thread.java:745) [?:1.8.0_74]
      Caused by: javax.mail.AuthenticationFailedException: 534-5.7.14 <https://accounts.google.com/signin/continue?sarp=x&xxx=x&xxx=xxxxxxxx
          534-5.7.14 xxxXXxxxXXXXXXXXXxXXXxXxXxXxXxXxXXXxXXXXX_XXxxxXXxXXXxXxXXxxXXxxXXXxxx
          534-5.7.14 xxxXXxx_XXXXXXXXXxXXXxXxXxXxXxXxXXXxXXXXXXXXxxxXXxXXXxXxXXxxXXxxXXXxxx
          534-5.7.14 xxxXXxxxXXXXXXXXXxXXXxXxXxXxXxXxXXXxXXXXXXXXxxxXXxXXXxXxXXxxXXxx-XXxxx
          534-5.7.14 xXX_xxxxXXXXXxXXXxXX-xxxXXXxX> Please log in via your web browser and
          534-5.7.14 then try again.
          534-5.7.14  Learn more at
          534 5.7.14  https://support.google.com/mail/answer/78754 b8sm33119713wjf.9 - gsmtp
          
      	at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:893) [javax.mail-1.5.4.jar:1.5.4]
      	at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:814) [javax.mail-1.5.4.jar:1.5.4]
      	at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:728) [javax.mail-1.5.4.jar:1.5.4]
      	at javax.mail.Service.connect(Service.java:386) [javax.mail-1.5.4.jar:1.5.4]
      	at javax.mail.Service.connect(Service.java:245) [javax.mail-1.5.4.jar:1.5.4]
      	at javax.mail.Service.connect(Service.java:194) [javax.mail-1.5.4.jar:1.5.4]
      	at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:174) [atlassian-mail-2.5.16.jar:?]
      	... 24 more

      Suggestion

      Make JIRA more secure to be able connect to Gmail without additional configuration

      Workaround

      1. Enabling access for less secure app in gmail seems to work for most of the cases
      2. If it doesn't work, as per the error message, please refer to the following link for more information about the error.
      3. If following that link doesn't work then please follow the steps in the following thread next

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              Unassigned Unassigned
              ywoo Yit Wei
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              Dates

                Created:
                Updated:
                Resolved: