Mail stuck in queue with "com.atlassian.mail.MailException: javax.mail.MessagingException: [EOF]"

[Mathew Miehling]

We recently started running into issues with our self-hosted JIRA server sending e-mails. 

Server: Atlassian JIRA Project Management Software (v7.7.0#77001-sha1:3be3151) 

I am attempting to route the outgoing mail through Amazon SES (same issue with O365 though), and I am seeing almost all mail build up in the outgoing/error queue in the JIRA admin.

Test e-mails always succeed, but it seems that normally mail eventually gets stopped up in the queue and can't send.

The error in the logs is: 

2018-11-05 19:03:43,485 ERROR [] Sending mailitem To='user@domain.com' Subject='(AB-XXXXX) Conflict upon installing 2019 Plug-In' From='null' FromName='Plug-in Engineer (JIRA)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='<JIRA.XXXXX.XXXXXXXXXXXXX@Atlassian.JIRA@Atlassian.JIRA>' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@38aebf52' MessageId='null' ExcludeSubjectPrefix=false' anonymous Mail Queue Service Error occurred in sending e-mail: To='user@domain.com' Subject='(AB-XXXXX) Conflict upon installing 2019 Plug-in' From='null' FromName='Plug-in Engineer(JIRA)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='<JIRA.XXXXX.XXXXXXXXXXXXX@Atlassian.JIRA@Atlassian.JIRA>' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@38aebf52' MessageId='null' ExcludeSubjectPrefix=false'
com.atlassian.mail.MailException: javax.mail.MessagingException: [EOF]
 at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:225) [atlassian-mail-2.8.6.jar:?]
 at com.atlassian.mail.queue.SingleMailQueueItem.send(SingleMailQueueItem.java:44) [atlassian-mail-2.8.6.jar:?]
 at com.atlassian.mail.queue.MailQueueImpl.sendBufferUnderLock(MailQueueImpl.java:103) [atlassian-mail-2.8.6.jar:?]
 at com.atlassian.mail.queue.MailQueueImpl.sendBuffer(MailQueueImpl.java:56) [atlassian-mail-2.8.6.jar:?]
 at com.atlassian.jira.mail.JiraMailQueue$1.apply(JiraMailQueue.java:51) [classes/:?]
 at com.atlassian.jira.mail.JiraMailQueue$1.apply(JiraMailQueue.java:48) [classes/:?]
 at com.atlassian.jira.util.velocity.DefaultVelocityRequestContextFactory.runWithStaticBaseUrl(DefaultVelocityRequestContextFactory.java:110) [classes/:?]
 at com.atlassian.jira.util.DefaultBaseUrl.runWithStaticBaseUrl(DefaultBaseUrl.java:50) [classes/:?]
 at com.atlassian.jira.mail.JiraMailQueue.sendBuffer(JiraMailQueue.java:48) [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: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:443) [atlassian-scheduler-caesium-1.3.3.jar:?]
 at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeLocalJob(CaesiumSchedulerService.java:410) [atlassian-scheduler-caesium-1.3.3.jar:?]
 at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService.executeQueuedJob(CaesiumSchedulerService.java:388) [atlassian-scheduler-caesium-1.3.3.jar:?]
 at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService$1.consume(CaesiumSchedulerService.java:285) [atlassian-scheduler-caesium-1.3.3.jar:?]
 at com.atlassian.scheduler.caesium.impl.CaesiumSchedulerService$1.consume(CaesiumSchedulerService.java:282) [atlassian-scheduler-caesium-1.3.3.jar:?]
 at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeJob(SchedulerQueueWorker.java:65) [atlassian-scheduler-caesium-1.3.3.jar:?]
 at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.executeNextJob(SchedulerQueueWorker.java:59) [atlassian-scheduler-caesium-1.3.3.jar:?]
 at com.atlassian.scheduler.caesium.impl.SchedulerQueueWorker.run(SchedulerQueueWorker.java:34) [atlassian-scheduler-caesium-1.3.3.jar:?]
 at java.lang.Thread.run(Thread.java:745) [?:1.8.0_65]
Caused by: javax.mail.MessagingException: [EOF]
 at com.sun.mail.smtp.SMTPTransport.issueCommand(SMTPTransport.java:2233) [javax.mail-1.5.6.jar:1.5.6]
 at com.sun.mail.smtp.SMTPTransport.helo(SMTPTransport.java:1617) [javax.mail-1.5.6.jar:1.5.6]
 at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:718) [javax.mail-1.5.6.jar:1.5.6]
 at javax.mail.Service.connect(Service.java:388) [javax.mail-1.5.6.jar:1.5.6]
 at javax.mail.Service.connect(Service.java:246) [javax.mail-1.5.6.jar:1.5.6]
 at javax.mail.Service.connect(Service.java:195) [javax.mail-1.5.6.jar:1.5.6]
 at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:185) [atlassian-mail-2.8.6.jar:?]
 ... 25 more

I've found a few threads suggesting that it may be that the mail host isn't set up to allow relaying from our JIRA server, but test e-mails from the JIRA system always succeed.

At this point, I'm thinking this is a 50/50 chance of being a config issue on my end or an issue on the AWS SES end. 

I was thinking that it could be rate limiting, but if I'm not mistaken you can actually see that in the JIRA log when it's a sending rate issue. We're also not sending nearly enough e-mails to reach out send limit with SES.

All of that being said, I've also opened a support ticket with AWS to have them check the SES side of things but I'm hoping someone here might see the stack trace and be able to point me in the right direction.

Thanks!

[Mathew Miehling]

Response from AWS says it is unlikely an issue with SES. The support person reviewed the configurations and the logs. There was one day where non-test e-mails were able to be sent, and they could see all of the test e-mails as well.