Jira notification emails intermittently fail to be sent due to the error "OAUTH2 asked for more" when using Gmail with Oauth 2.0

Summary

The purpose of this article is to describe a scenario where notification emails intermittently fail to be sent, when the Jira application is configured with a GMAIL server as the outgoing mail server along with the Oauth 2.0 authentication method.

Environment

• Jira Software Server/Data Center on 9.2.0 or any higher version

• Jira Service Management Server / Data Center on 5.2.0 or any higher version

Diagnosis

• Jira is configured in the ⚙ > System > Outgoing Mail page with a GMAIL server as the outgoing mail server along with the Oauth 2.0 authentication method, as per the documentation Configuring an SMTP mail server to send notifications

• Notification emails are intermittently piling up in the Mail Error Queue, which can be seen in the ⚙ > System > Mail Queue page (some emails get to be sent, and some emails are failing to be sent and end up in this queue):

• The error "OAUTH2 asked for more" is found in the atlassian-outgoing-mail-jira.log file:

  1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 2024-08-20 08:45:00,640+0000 ERROR [] Sending mailitem To='someemail@gmail.com' Subject='(SCRUM2-3) test 2' From='null' FromName='admin (Jira)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='<JIRA.10201.1724055282000@Atlassian.JIRA>' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@72d09ac0' MessageId='null' ExcludeSubjectPrefix=false' anonymous Mail Queue Service [c.a.mail.queue.MailQueueImpl] Error occurred in sending e-mail: To='someemail@gmail.com' Subject='(SCRUM2-3) test 2' From='null' FromName='admin (Jira)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='<JIRA.10201.1724055282000@Atlassian.JIRA>' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@72d09ac0' MessageId='null' ExcludeSubjectPrefix=false' com.atlassian.mail.MailException: javax.mail.AuthenticationFailedException: 334 eyJzdGF0dXMiOiI0MDAiLCJzY2hlbWVzIjoiQmVhcmVyIiwic2NvcGUiOiJodHRwczovL21haWwuZ29vZ2xlLmNvbS8ifQ== ; nested exception is: javax.mail.AuthenticationFailedException: OAUTH2 asked for more 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:?] at com.atlassian.jira.mail.JiraMailQueue.lambda$sendAndUpdateIpdMetric$0(JiraMailQueue.java:154) [classes/:?] at com.atlassian.jira.util.velocity.DefaultVelocityRequestContextFactory.runWithStaticBaseUrl(DefaultVelocityRequestContextFactory.java:110) [classes/:?] at com.atlassian.jira.util.DefaultBaseUrl.runWithStaticBaseUrl(DefaultBaseUrl.java:56) [classes/:?] at com.atlassian.jira.mail.JiraMailQueue.sendAndUpdateIpdMetric(JiraMailQueue.java:153) [classes/:?] at com.atlassian.jira.mail.JiraMailQueue.sendBuffer(JiraMailQueue.java:70) [classes/:?] at com.atlassian.jira.service.services.mail.MailQueueService.run(MailQueueService.java:21) [classes/:?] at com.atlassian.jira.service.JiraServiceContainerImpl.run(JiraServiceContainerImpl.java:68) [classes/:?] at com.atlassian.jira.service.ServiceRunner.runService(ServiceRunner.java:62) [classes/:?] at com.atlassian.jira.service.ServiceRunner.runServiceId(ServiceRunner.java:44) [classes/:?] at com.atlassian.jira.service.ServiceRunner.runJob(ServiceRunner.java:32) [classes/:?] at com.atlassian.scheduler.core.JobLauncher.runJob(JobLauncher.java:134) [atlassian-scheduler-core-4.2.1.jar:?] at com.atlassian.scheduler.core.JobLauncher.launchAndBuildResponse(JobLauncher.java:106) [atlassian-scheduler-core-4.2.1.jar:?] at com.atlassian.scheduler.core.JobLauncher.launch(JobLauncher.java:90) [atlassian-scheduler-core-4.2.1.jar:?] at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.launchJob(CaesiumSchedulerService.java:500) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeLocalJobWithRetryOnFailure(CaesiumSchedulerService.java:463) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeQueuedJob(CaesiumSchedulerService.java:413) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeJob(SchedulerQueueWorker.java:66) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeNextJob(SchedulerQueueWorker.java:60) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.run(SchedulerQueueWorker.java:35) [atlassian-scheduler-caesium-3.1.4.jar:?] at java.base/java.lang.Thread.run(Thread.java:840) [?:?] Caused by: javax.mail.AuthenticationFailedException: 334 eyJzdGF0dXMiOiI0MDAiLCJzY2hlbWVzIjoiQmVhcmVyIiwic2NvcGUiOiJodHRwczovL21haWwuZ29vZ2xlLmNvbS8ifQ== ; nested exception is: javax.mail.AuthenticationFailedException: OAUTH2 asked for more at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:942) [jakarta.mail-1.6.7.jar:1.6.7] at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:858) [jakarta.mail-1.6.7.jar:1.6.7] at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:762) [jakarta.mail-1.6.7.jar:1.6.7] at javax.mail.Service.connect(Service.java:342) [jakarta.mail-api-1.6.7.jar:1.6.7] at javax.mail.Service.connect(Service.java:222) [jakarta.mail-api-1.6.7.jar:1.6.7] at javax.mail.Service.connect(Service.java:243) [jakarta.mail-api-1.6.7.jar:1.6.7] at com.atlassian.mail.auth.JiraOauth2AuthenticationContext.connectUsingToken(JiraOauth2AuthenticationContext.java:97) [classes/:?] at com.atlassian.mail.auth.JiraOauth2AuthenticationContext.recoverOrRethrow(JiraOauth2AuthenticationContext.java:84) [classes/:?] at com.atlassian.mail.auth.JiraOauth2AuthenticationContext.connectService(JiraOauth2AuthenticationContext.java:75) [classes/:?] at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:215) [atlassian-mail-6.0.2.jar:?] ... 24 more Caused by: javax.mail.AuthenticationFailedException: OAUTH2 asked for more at com.sun.mail.smtp.SMTPTransport$OAuth2Authenticator.doAuth(SMTPTransport.java:1121) [jakarta.mail-1.6.7.jar:1.6.7] at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:924) [jakarta.mail-1.6.7.jar:1.6.7] ... 33 more

• If the authentication method is changed to the Basic Authentication method in the ⚙ > System > Outgoing Mail page, a different error "454-4.7.0 Too many login attempts" is found in the atlassian-outgoing-mail-jira.log file:

  1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 2024-08-20 13:24:40,652+0000 ERROR [] Sending mailitem To='someemail@gmail.com' Subject='(SCRUM2-3) test 2' From='null' FromName='admin (Jira)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='null' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@698d4dbf' MessageId='null' ExcludeSubjectPrefix=false' anonymous Mail Queue Service [c.a.mail.queue.MailQueueImpl] Error occurred in sending e-mail: To='someemail@gmail.com' Subject='(SCRUM2-3) test 2' From='null' FromName='admin (Jira)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='<JIRA.10201.1724055282000@Atlassian.JIRA>' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@698d4dbf' MessageId='null' ExcludeSubjectPrefix=false' com.atlassian.mail.MailException: javax.mail.AuthenticationFailedException: 454-4.7.0 Too many login attempts, please try again later. For more information, 454-4.7.0 go to 454 4.7.0 https://support.google.com/mail/answer/7126229 a640c23a62f3a-a83838cfe3asm762728666b.86 - 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:?] at com.atlassian.jira.mail.JiraMailQueue.lambda$sendAndUpdateIpdMetric$0(JiraMailQueue.java:154) [classes/:?] at com.atlassian.jira.util.velocity.DefaultVelocityRequestContextFactory.runWithStaticBaseUrl(DefaultVelocityRequestContextFactory.java:110) [classes/:?] at com.atlassian.jira.util.DefaultBaseUrl.runWithStaticBaseUrl(DefaultBaseUrl.java:56) [classes/:?] at com.atlassian.jira.mail.JiraMailQueue.sendAndUpdateIpdMetric(JiraMailQueue.java:153) [classes/:?] at com.atlassian.jira.mail.JiraMailQueue.sendBuffer(JiraMailQueue.java:70) [classes/:?] at com.atlassian.jira.service.services.mail.MailQueueService.run(MailQueueService.java:21) [classes/:?] at com.atlassian.jira.service.JiraServiceContainerImpl.run(JiraServiceContainerImpl.java:68) [classes/:?] at com.atlassian.jira.service.ServiceRunner.runService(ServiceRunner.java:62) [classes/:?] at com.atlassian.jira.service.ServiceRunner.runServiceId(ServiceRunner.java:44) [classes/:?] at com.atlassian.jira.service.ServiceRunner.runJob(ServiceRunner.java:32) [classes/:?] at com.atlassian.scheduler.core.JobLauncher.runJob(JobLauncher.java:134) [atlassian-scheduler-core-4.2.1.jar:?] at com.atlassian.scheduler.core.JobLauncher.launchAndBuildResponse(JobLauncher.java:106) [atlassian-scheduler-core-4.2.1.jar:?] at com.atlassian.scheduler.core.JobLauncher.launch(JobLauncher.java:90) [atlassian-scheduler-core-4.2.1.jar:?] at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.launchJob(CaesiumSchedulerService.java:500) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeLocalJobWithRetryOnFailure(CaesiumSchedulerService.java:463) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeQueuedJob(CaesiumSchedulerService.java:413) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeJob(SchedulerQueueWorker.java:66) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeNextJob(SchedulerQueueWorker.java:60) [atlassian-scheduler-caesium-3.1.4.jar:?] at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.run(SchedulerQueueWorker.java:35) [atlassian-scheduler-caesium-3.1.4.jar:?] at java.base/java.lang.Thread.run(Thread.java:840) [?:?] Caused by: javax.mail.AuthenticationFailedException: 454-4.7.0 Too many login attempts, please try again later. For more information, 454-4.7.0 go to 454 4.7.0 https://support.google.com/mail/answer/7126229 a640c23a62f3a-a83838cfe3asm762728666b.86 - gsmtp at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:947) [jakarta.mail-1.6.7.jar:1.6.7] at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:858) [jakarta.mail-1.6.7.jar:1.6.7] at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:762) [jakarta.mail-1.6.7.jar:1.6.7] at javax.mail.Service.connect(Service.java:364) [jakarta.mail-api-1.6.7.jar:1.6.7] at javax.mail.Service.connect(Service.java:222) [jakarta.mail-api-1.6.7.jar:1.6.7] at javax.mail.Service.connect(Service.java:243) [jakarta.mail-api-1.6.7.jar:1.6.7] at com.atlassian.mail.server.InternalAuthenticationContext.connectService(InternalAuthenticationContext.java:35) [atlassian-mail-6.0.2.jar:?] at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:215) [atlassian-mail-6.0.2.jar:?] ... 24 more

Cause

The Jira application fails to send the notifications due to the fact that the Gmail Server Throttling Limit was reached (the Jira application attempted to send more emails that what is accepted by the GMAIL SMTP server). Depending on the authentication method that is used by the Outgoing Mail Server configuration, a different error is thrown in the Jira Outgoing Mail Logs:

• In the case where Oauth 2.0 is used as the authentication method, the error OAUTH2 asked for more is thrown

• In the case where the Basic Authentication (username/password) is used as the authentication method, the error 454-4.7.0 Too many login attempts is thrown instead

You can find more information about the error code 454-4.7.0 in Gmail SMTP errors and codes.

Solution

Since the throttling limit is coming from the GMAIL SMTP Server side, we recommend reaching out to your GMAIL Server administrator or to the Google Support Team for further assistance, and to see if it is possible to increase this limit.

We're also tracking this issue in the feature request: JRASERVER-38806 - Support throttling to handle Google SMTP error 454 4.7.0 Too many login attempts, please try again later.