some times outgoing email error

Question

dear community, i have a strange problem. my Jira Service Desk works great, incoming and outgoing emails are no problem. Only some times per month on single tickets, the outgoing email is delivered to the exchange server, so the enduser receive the information, but my Jira Server resend the email because of timeout errors. next minute the Jira server resend the email, the enduser receive it, on the server again an error. This loop is up to 15 minutes, so the enduser receive the message 15 times... any idea what could be the problem? br Hermann 2017-12-28 18:36:10,040 ERROR [] Sending mailitem To='my.user@mydomain.at' Subject='HSITSD-119 Intranet geht nicht in Firefox' From='null' FromName='Hermann Lämmerer' Cc='null' Bcc='null' ReplyTo='itservices.vie@mydomain.at' InReplyTo='' MimeType='text/plain' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@5d12b940' MessageId='null' ExcludeSubjectPrefix=true' anonymous Mail Queue Service Error occurred in sending e-mail: To='my.user@mydomain.at' Subject='HSITSD-119 Intranet geht nicht in Firefox' From='null' FromName='Hermann Lämmerer' Cc='null' Bcc='null' ReplyTo='itservices.vie@mydomain.at' InReplyTo='' MimeType='text/plain' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@5d12b940' MessageId='null' ExcludeSubjectPrefix=true' 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.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:61) [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_102] Caused by: javax.mail.MessagingException: Exception reading response; nested exception is: java.net.SocketTimeoutException: Read timed out at com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2369) [javax.mail-1.5.6.jar:1.5.6] at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2246) [javax.mail-1.5.6.jar:1.5.6] at com.sun.mail.smtp.SMTPTransport.finishData(SMTPTransport.java:2045) [javax.mail-1.5.6.jar:1.5.6] at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1260) [javax.mail-1.5.6.jar:1.5.6] at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendMimeMessage(SMTPMailServerImpl.java:245) [atlassian-mail-2.8.6.jar:?] at com.atlassian.mail.server.managers.EventAwareSMTPMailServer.sendMimeMessage(EventAwareSMTPMailServer.java:25) [classes/:?] at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:187) [atlassian-mail-2.8.6.jar:?] ... 25 more Caused by: java.net.SocketTimeoutException: Read timed out at java.net.SocketInputStream.socketRead0(Native Method) [?:1.8.0_102] at java.net.SocketInputStream.socketRead(SocketInputStream.java:116) [?:1.8.0_102] at java.net.SocketInputStream.read(SocketInputStream.java:170) [?:1.8.0_102] at java.net.SocketInputStream.read(SocketInputStream.java:141) [?:1.8.0_102] at com.sun.mail.util.TraceInputStream.read(TraceInputStream.java:124) [javax.mail-1.5.6.jar:1.5.6] at java.io.BufferedInputStream.fill(BufferedInputStream.java:246) [?:1.8.0_102] at java.io.BufferedInputStream.read(BufferedInputStream.java:265) [?:1.8.0_102] at com.sun.mail.util.LineInputStream.readLine(LineInputStream.java:92) [javax.mail-1.5.6.jar:1.5.6] at com.sun.mail.smtp.SMTPTransport.readServerResponse(SMTPTransport.java:2349) [javax.mail-1.5.6.jar:1.5.6] ... 31 more

Hermann Lämmerer · Answer

We changed the timeout setting from 10000 to 30000, until now no new errors/timeout, thx for the support!

somethingblue · Answer

Hi Hermann,

The behavior you're describing sounds like the second scenario in Read timed out error when sending outbound mail from JIRA applications:

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.

Resolution

Increase the time out value for the mailbox(s) affected as in our Configuring JIRA's 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.

If you are using a DigitalOcean Droplet or Amazon take a look at Read timed out error when sending outbound mail from JIRA applications as you'll need to contact the provider for further assistance from their end.

Cheers,

Branden