java.net.SocketException: Permission denied: connect for sending emails

[Melvin Arroyo]

I have upgraded from JIRA 6.2 to JIRA 7, but after a week we started getting this error I will list below. I have 2-3 questions and i may have found the problem, but will still post here.

Above is the error I get when testing my connection. I recently built a test environment and i am not getting this error email is working fine on version 7 Here is the error from the log:

2016-02-23 15:42:01,144 ERROR [] Sending mailitem To='removed@me.com' Subject='(IR-3208) Updating participant name in Name Card does not trigger Participant Tile on navigation page until manual page refresh' From='null' FromName='Username (JIRA)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='<JIRA.17210.1456259712000@Atlassian.JIRA>' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@4167cb' MessageId='null' anonymous Mail Queue Service Error occurred in sending e-mail: To='removed@me.com' Subject='(IR-3208) Updating participant name in Name Card does not trigger Participant Tile on navigation page until manual page refresh' From='null' FromName='Username (JIRA)' Cc='null' Bcc='null' ReplyTo='null' InReplyTo='<JIRA.17210.1456259712000@Atlassian.JIRA>' MimeType='text/html' Encoding='UTF-8' Multipart='javax.mail.internet.MimeMultipart@4167cb' MessageId='null'
com.atlassian.mail.MailException: javax.mail.MessagingException: Could not connect to SMTP host: myhost.com, port: 25;
nested exception is:
java.net.SocketException: Permission denied: connect
at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:213) [atlassian-mail-2.5.6.jar:?]
at com.atlassian.mail.queue.SingleMailQueueItem.send(SingleMailQueueItem.java:44) [atlassian-mail-2.5.6.jar:?]
at com.atlassian.mail.queue.MailQueueImpl.sendBuffer(MailQueueImpl.java:66) [atlassian-mail-2.5.6.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:26) [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_51]
Caused by: javax.mail.MessagingException: Could not connect to SMTP host: mybox.com, port: 25;
nested exception is:
java.net.SocketException: Permission denied: connect
at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1972) [mail-1.4.5.jar:1.4.5]
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:642) [mail-1.4.5.jar:1.4.5]
at javax.mail.Service.connect(Service.java:317) [mail-1.4.5.jar:1.4.5]
at javax.mail.Service.connect(Service.java:176) [mail-1.4.5.jar:1.4.5]
at javax.mail.Service.connect(Service.java:125) [mail-1.4.5.jar:1.4.5]
at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:173) [atlassian-mail-2.5.6.jar:?]

Question #1 initially was... do i need to update my java? i'm using 1.4.2, but i see in JIRA 7 I needed 1.8 and I don't get this error, I see this line

at javax.mail.Service.connect(Service.java:317) [mail-1.4.5.jar:1.4.5]

I updated to 1.8 but I am still getting the error:

An error has occurred with sending the test email:
com.atlassian.mail.MailException: javax.mail.MessagingException: Could not connect to SMTP host: mybox.com, port: 25;
nested exception is:
java.net.SocketException: Permission denied: connect
at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:213)
at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:150)
at com.atlassian.jira.plugins.mail.webwork.SendTestMail.doExecute(SendTestMail.java:107)
at webwork.action.ActionSupport.execute(ActionSupport.java:165)
at com.atlassian.jira.action.JiraActionSupport.execute(JiraActionSupport.java:63)
at webwork.interceptor.DefaultInterceptorChain.proceed(DefaultInterceptorChain.java:39)
at webwork.interceptor.NestedInterceptorChain.proceed(NestedInterceptorChain.java:31)
at webwork.interceptor.ChainedInterceptor.intercept(ChainedInterceptor.java:16)
at webwork.interceptor.DefaultInterceptorChain.proceed(DefaultInterceptorChain.java:35)
at webwork.dispatcher.GenericDispatcher.executeAction(GenericDispatcher.java:225)

I seen in another post that i could delete my SMPT settings and redo them and it would work, but i have over 200+ messages in the error que that need to be send/routed to developers that cant be lost.

Question #2 Will the messages be deleted when I redo the settings?
Question #3 where are these que'd messages stored? in the SQL database or locally in the Atlassian home install area?

NOTE: Again...  In my test environment which is a fresh install the same settings for mail work just fine, in this upgrade from 6.2 after a week stopped working.

[Melvin Arroyo]

Update:  I upgraded to version 7.0.10 and initially it fixed my issue above, but now a few days later its not working.  My test environment is working just fine no issues.