Issue in Send Test Email after configuring outgoing email server

Question

I have done configuration of outgoing email server using smtp.google.com and test connection is suceeded, when i try to send test email the following log details displayed in email log, kindly let me know the exact issue,

an error has occurred with sending the test email:
com.atlassian.mail.MailException: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. n22sm144180435pfh.166 - gsmtp

at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:225)
at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:162)
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)

Software HOD · Answer

I have downloaded the mail-x.x.x.jar and activation-x.x.x.jar and placed into Atlassian\JIRA\lib folder

now I am receiving the following error, when sending the test email,

An error has occurred with sending the test email:
com.atlassian.mail.MailException: javax.naming.NamingException: Unexpected exception resolving reference [Root exception is java.lang.NullPointerException]
at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:221)
at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:162)
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)

Software HOD · Answer

Thank you Fazila, I do not find the mail-x.x.x.jar under "Atlassian\JIRA\atlassian-jira\WEB-INF\lib"

im using JIRA Software Version 7.12.1 , Kindly guide me how to solve the issue.

Fazila Ashraf · Answer

Hi @Software HOD

There is an atlassian KB on this for confluence -> https://confluence.atlassian.com/confkb/unable-to-send-email-due-to-smtpsendfailedexception-530-5-7-0-must-issue-a-starttls-command-first-316637646.html

Same would apply for jira also. Hope this helps in resolving the issue