Details
-
Bug
-
Resolution: Not a bug
-
Low
-
None
-
7.0.0
-
7
-
Description
Problem Definition
If you have 2-Step Verification for Gmail account that you are trying to setup SMTP for, when you test connection you will get.
Unfortunately no connection was possible. Review the errors below and rectify:
AuthenticationFailedException: 534-5.7.9 Application-specific password required. Learn more at 534 5.7.9 https://support.google.com/accounts/answer/185833 by3sm13205108pab.39 - gsmtp
In atlassian-jira.log at the same time:
2016-02-19 10:11:00,367 http-nio-8787-exec-6 ERROR sam 610x307x1 aqhz1w 0:0:0:0:0:0:0:1 /secure/admin/VerifySmtpServerConnection!add.jspa [c.a.j.p.mail.webwork.VerifyMailServer] Unable to connect to the server at smtp.gmail.com due to the following exception: javax.mail.AuthenticationFailedException: 534-5.7.9 Application-specific password required. Learn more at
534 5.7.9 https://support.google.com/accounts/answer/185833 by3sm13205108pab.39 - gsmtp
Steps To Reproduce
- Enable 2-Step Verification for your Gmail account
- Set up your SMTP (outgoing mail) with the Gamil account
Expected Result
Test Connection and Test mail should result in success
Actual Result
Both tests fail
More Details
Referring to the link at https://support.google.com/accounts/answer/185833 asks to enable app password.
Setting up Custom app password, makes you enable to have successful connection test once.
Testing again (without entering app password) generates below error, however, keying in the app password gives you the successful result on connection test.
Unfortunately no connection was possible. Review the errors below and rectify:
AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at 535 5.7.8 https://support.google.com/mail/answer/14257 xu1sm13243659pab.31 - gsmtp
In atlassian-jira.log at the same time:
2016-02-19 10:05:00,128 http-nio-8787-exec-16 ERROR sam 604x238x1 aqhz1w 0:0:0:0:0:0:0:1 /secure/admin/VerifySmtpServerConnection!update.jspa [c.a.j.p.mail.webwork.VerifyMailServer] Unable to connect to the server at smtp.gmail.com due to the following exception: javax.mail.AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at
535 5.7.8 https://support.google.com/mail/answer/14257 t12sm13234927pfa.54 - gsmtp
But referring to Send Test Mail option. The connection fails and Test mail can't be sent by:
An error has occurred with sending the test email: com.atlassian.mail.MailException: javax.mail.AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at 535 5.7.8 https://support.google.com/mail/answer/14257 i13sm13210356pfi.95 - gsmtp 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:67) 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) at webwork.dispatcher.GenericDispatcher.executeAction(GenericDispatcher.java:154) at com.atlassian.jira.web.dispatcher.JiraWebworkActionDispatcher.service(JiraWebworkActionDispatcher.java:152) at javax.servlet.http.HttpServlet.service(HttpServlet.java:725) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:291) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:52) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.steps.ChainedFilterStepRunner.doFilter(ChainedFilterStepRunner.java:86) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.XContentTypeOptionsNoSniffFilter.doFilter(XContentTypeOptionsNoSniffFilter.java:22) at com.atlassian.core.filters.AbstractHttpFilter.doFilter(AbstractHttpFilter.java:31) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.core.filters.HeaderSanitisingFilter.doFilter(HeaderSanitisingFilter.java:44) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:46) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.jira.onboarding.postsetup.ui.PostSetupAnnouncementsFilter.doFilter(PostSetupAnnouncementsFilter.java:61) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.jira.tzdetect.IncludeResourcesFilter.doFilter(IncludeResourcesFilter.java:85) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.jira.baseurl.IncludeResourcesFilter.doFilter(IncludeResourcesFilter.java:38) at com.atlassian.core.filters.AbstractHttpFilter.doFilter(AbstractHttpFilter.java:31) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.applinks.core.rest.context.ContextFilter.doFilter(ContextFilter.java:26) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.applinks.core.rest.context.ContextFilter.doFilter(ContextFilter.java:26) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.applinks.core.rest.context.ContextFilter.doFilter(ContextFilter.java:26) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.applinks.core.rest.context.ContextFilter.doFilter(ContextFilter.java:26) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.applinks.core.rest.context.ContextFilter.doFilter(ContextFilter.java:26) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.servicedesk.internal.web.RedirectExternalCustomerToPortalFilter.doFilter(RedirectExternalCustomerToPortalFilter.scala:18) at com.atlassian.core.filters.AbstractHttpFilter.doFilter(AbstractHttpFilter.java:31) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.greenhopper.jira.filters.ClassicBoardRouter.doFilter(ClassicBoardRouter.java:59) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.mywork.client.filter.ServingRequestsFilter.doFilter(ServingRequestsFilter.java:37) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.prettyurls.filter.PrettyUrlsSiteMeshFixupFilter.doFilter(PrettyUrlsSiteMeshFixupFilter.java:36) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.prettyurls.filter.PrettyUrlsDispatcherFilter.doFilter(PrettyUrlsDispatcherFilter.java:60) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.prettyurls.filter.PrettyUrlsSiteMeshFilter.doFilter(PrettyUrlsSiteMeshFilter.java:92) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.prettyurls.filter.PrettyUrlsMatcherFilter.doFilter(PrettyUrlsMatcherFilter.java:56) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.labs.botkiller.BotKillerFilter.doFilter(BotKillerFilter.java:36) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.ServletFilterModuleContainerFilter.doFilter(ServletFilterModuleContainerFilter.java:77) at com.atlassian.plugin.servlet.filter.ServletFilterModuleContainerFilter.doFilter(ServletFilterModuleContainerFilter.java:63) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.accesslog.AccessLogFilter.executeRequest(AccessLogFilter.java:100) at com.atlassian.jira.web.filters.accesslog.AccessLogFilter.doFilter(AccessLogFilter.java:84) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.security.xsrf.XsrfTokenAdditionRequestFilter.doFilter(XsrfTokenAdditionRequestFilter.java:54) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.opensymphony.sitemesh.webapp.SiteMeshFilter.obtainContent(SiteMeshFilter.java:181) at com.opensymphony.sitemesh.webapp.SiteMeshFilter.doFilter(SiteMeshFilter.java:85) at com.atlassian.jira.web.filters.SitemeshPageFilter.doFilter(SitemeshPageFilter.java:124) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.pagebuilder.PageBuilderFilter.doFilter(PageBuilderFilter.java:90) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.CommittedResponseHtmlErrorRecoveryFilter.doFilter(CommittedResponseHtmlErrorRecoveryFilter.java:63) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:46) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.prettyurls.filter.PrettyUrlsCombinedMatchDispatcherFilter.doFilter(PrettyUrlsCombinedMatchDispatcherFilter.java:61) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.ServletFilterModuleContainerFilter.doFilter(ServletFilterModuleContainerFilter.java:77) at com.atlassian.plugin.servlet.filter.ServletFilterModuleContainerFilter.doFilter(ServletFilterModuleContainerFilter.java:63) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.seraph.filter.SecurityFilter.doFilter(SecurityFilter.java:242) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.security.auth.trustedapps.filter.TrustedApplicationsFilter.doFilter(TrustedApplicationsFilter.java:103) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.seraph.filter.BaseLoginFilter.doFilter(BaseLoginFilter.java:148) at com.atlassian.jira.web.filters.JiraLoginFilter.doFilter(JiraLoginFilter.java:70) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:46) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.oauth.serviceprovider.internal.servlet.OAuthFilter.doFilter(OAuthFilter.java:79) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.prettyurls.filter.PrettyUrlsCombinedMatchDispatcherFilter.doFilter(PrettyUrlsCombinedMatchDispatcherFilter.java:61) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.ServletFilterModuleContainerFilter.doFilter(ServletFilterModuleContainerFilter.java:77) at com.atlassian.plugin.servlet.filter.ServletFilterModuleContainerFilter.doFilter(ServletFilterModuleContainerFilter.java:63) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.util.profiling.filters.ProfilingFilter.doFilter(ProfilingFilter.java:99) at com.atlassian.jira.web.filters.JIRAProfilingFilter.doFilter(JIRAProfilingFilter.java:19) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.johnson.filters.AbstractJohnsonFilter.doFilter(AbstractJohnsonFilter.java:59) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at org.tuckey.web.filters.urlrewrite.RuleChain.handleRewrite(RuleChain.java:176) at org.tuckey.web.filters.urlrewrite.RuleChain.doRules(RuleChain.java:145) at org.tuckey.web.filters.urlrewrite.UrlRewriter.processRequest(UrlRewriter.java:92) at org.tuckey.web.filters.urlrewrite.UrlRewriteFilter.doFilter(UrlRewriteFilter.java:394) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:46) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.analytics.client.filter.JiraAnalyticsFilter.doFilter(JiraAnalyticsFilter.java:41) at com.atlassian.analytics.client.filter.AbstractHttpFilter.doFilter(AbstractHttpFilter.java:32) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:70) at com.atlassian.prettyurls.filter.PrettyUrlsCombinedMatchDispatcherFilter.doFilter(PrettyUrlsCombinedMatchDispatcherFilter.java:61) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:78) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.ServletFilterModuleContainerFilter.doFilter(ServletFilterModuleContainerFilter.java:77) at com.atlassian.plugin.servlet.filter.ServletFilterModuleContainerFilter.doFilter(ServletFilterModuleContainerFilter.java:63) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.steps.ChainedFilterStepRunner.doFilter(ChainedFilterStepRunner.java:86) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.core.filters.cache.AbstractCachingFilter.doFilter(AbstractCachingFilter.java:33) at com.atlassian.core.filters.AbstractHttpFilter.doFilter(AbstractHttpFilter.java:31) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.core.filters.encoding.AbstractEncodingFilter.doFilter(AbstractEncodingFilter.java:41) at com.atlassian.core.filters.AbstractHttpFilter.doFilter(AbstractHttpFilter.java:31) at com.atlassian.jira.web.filters.PathMatchingEncodingFilter.doFilter(PathMatchingEncodingFilter.java:49) at com.atlassian.core.filters.AbstractHttpFilter.doFilter(AbstractHttpFilter.java:31) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.startup.JiraStartupChecklistFilter.doFilter(JiraStartupChecklistFilter.java:79) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.MultipartBoundaryCheckFilter.doFilter(MultipartBoundaryCheckFilter.java:41) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.steps.ChainedFilterStepRunner.doFilter(ChainedFilterStepRunner.java:86) at com.atlassian.jira.web.filters.JiraFirstFilter.doFilter(JiraFirstFilter.java:62) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.gzipfilter.GzipFilter.doFilterInternal(GzipFilter.java:115) at com.atlassian.gzipfilter.GzipFilter.doFilter(GzipFilter.java:92) at com.atlassian.jira.web.filters.gzip.JiraGzipFilter.doFilter(JiraGzipFilter.java:56) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:239) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:219) at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:106) at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:142) at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:79) at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:88) at org.apache.catalina.valves.AbstractAccessLogValve.invoke(AbstractAccessLogValve.java:610) at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:516) at org.apache.coyote.http11.AbstractHttp11Processor.process(AbstractHttp11Processor.java:1086) at org.apache.coyote.AbstractProtocol$AbstractConnectionHandler.process(AbstractProtocol.java:659) at org.apache.coyote.http11.Http11NioProtocol$Http11ConnectionHandler.process(Http11NioProtocol.java:223) at org.apache.tomcat.util.net.NioEndpoint$SocketProcessor.doRun(NioEndpoint.java:1558) at org.apache.tomcat.util.net.NioEndpoint$SocketProcessor.run(NioEndpoint.java:1515) at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1142) at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:617) at org.apache.tomcat.util.threads.TaskThread$WrappingRunnable.run(TaskThread.java:61) at java.lang.Thread.run(Thread.java:745) Caused by: javax.mail.AuthenticationFailedException: 535-5.7.8 Username and Password not accepted. Learn more at 535 5.7.8 https://support.google.com/mail/answer/14257 i13sm13210356pfi.95 - gsmtp at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:823) at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:756) at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:673) at javax.mail.Service.connect(Service.java:317) at javax.mail.Service.connect(Service.java:176) at javax.mail.Service.connect(Service.java:125) at com.atlassian.mail.server.impl.SMTPMailServerImpl.sendWithMessageId(SMTPMailServerImpl.java:173) ... 219 more
Apparently, some apps and devices use less secure sign-in technology, which makes your account more vulnerable. You can turn off access for these apps, which is recommended, or turn on access if you want to use them despite the risks.
However, this setting is not available for accounts with 2-Step Verification enabled. Such accounts require an application-specific password for less secure apps access.