Hi Everyone we are using Jira 5.0.6 and our email stopped working over the weekend. I have verified that other servers can send emails (confluence) using the exact same settings to the email server (only 1 email server). The error I am getting is a java error on Jira. I am not to familiar with Java and was hoping someone can tell me what is going wrong. Even if the answer is that I should just restart Jira. Here is the error.
An error has occurred with sending the test email: com.atlassian.mail.MailException: javax.mail.MessagingException: Could not convert socket to TLS; nested exception is: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: timestamp check failed at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:193) 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:82) 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:205) at webwork.dispatcher.GenericDispatcher.executeAction(GenericDispatcher.java:143) at com.atlassian.jira.web.dispatcher.JiraWebworkActionDispatcher.service(JiraWebworkActionDispatcher.java:151) at javax.servlet.http.HttpServlet.service(HttpServlet.java:717) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:290) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.steps.ChainedFilterStepRunner.doFilter(ChainedFilterStepRunner.java:78) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) 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:235) 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:66) at com.atlassian.labs.botkiller.BotKillerFilter.doFilter(BotKillerFilter.java:36) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:74) at com.atlassian.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:42) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:66) at com.atlassian.applinks.core.rest.context.ContextFilter.doFilter(ContextFilter.java:25) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:74) 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:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.accesslog.AccessLogFilter.executeRequest(AccessLogFilter.java:104) at com.atlassian.jira.web.filters.accesslog.AccessLogFilter.doFilter(AccessLogFilter.java:88) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) 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:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.opensymphony.sitemesh.webapp.SiteMeshFilter.obtainContent(SiteMeshFilter.java:129) at com.opensymphony.sitemesh.webapp.SiteMeshFilter.doFilter(SiteMeshFilter.java:77) at com.atlassian.jira.web.filters.SitemeshPageFilter.doFilter(SitemeshPageFilter.java:124) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) 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.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:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.seraph.filter.SecurityFilter.doFilter(SecurityFilter.java:234) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.security.auth.trustedapps.filter.TrustedApplicationsFilter.doFilter(TrustedApplicationsFilter.java:98) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.seraph.filter.BaseLoginFilter.doFilter(BaseLoginFilter.java:157) at com.atlassian.jira.web.filters.JiraLoginFilter.doFilter(JiraLoginFilter.java:70) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) 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:66) at com.atlassian.oauth.serviceprovider.internal.servlet.OAuthFilter.doFilter(OAuthFilter.java:71) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:74) 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:235) 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:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.johnson.filters.AbstractJohnsonFilter.doFilter(AbstractJohnsonFilter.java:71) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at org.tuckey.web.filters.urlrewrite.UrlRewriteFilter.doFilter(UrlRewriteFilter.java:350) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.gzipfilter.GzipFilter.doFilterInternal(GzipFilter.java:81) at com.atlassian.gzipfilter.GzipFilter.doFilter(GzipFilter.java:51) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) 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:66) at com.sysbliss.jira.plugins.workflow.servlet.JWDSendRedirectFilter.doFilter(JWDSendRedirectFilter.java:25) at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter.doFilter(DelegatingPluginFilter.java:74) 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:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.steps.ChainedFilterStepRunner.doFilter(ChainedFilterStepRunner.java:78) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) 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:235) 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:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.monitor.ActiveRequestsFilter$PassToChainFilterFunc.doFilter(ActiveRequestsFilter.java:346) at com.atlassian.jira.web.monitor.ActiveRequestsFilter$DebugLogFilterFunc.doFilter(ActiveRequestsFilter.java:463) at com.atlassian.jira.web.monitor.ActiveRequestsFilter.doFilter(ActiveRequestsFilter.java:173) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.startup.JiraStartupChecklistFilter.doFilter(JiraStartupChecklistFilter.java:75) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.multitenant.servlet.MultiTenantServletFilter.doFilter(MultiTenantServletFilter.java:91) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at com.atlassian.jira.web.filters.steps.ChainedFilterStepRunner.doFilter(ChainedFilterStepRunner.java:78) at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235) at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206) at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:233) at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:191) at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:127) at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:102) at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:109) at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:554) at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:298) at org.apache.coyote.http11.Http11Processor.process(Http11Processor.java:859) at org.apache.coyote.http11.Http11Protocol$Http11ConnectionHandler.process(Http11Protocol.java:588) at org.apache.tomcat.util.net.JIoEndpoint$Worker.run(JIoEndpoint.java:489) at java.lang.Thread.run(Thread.java:662) Caused by: javax.mail.MessagingException: Could not convert socket to TLS; nested exception is: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: timestamp check failed at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1918) at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:652) 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.send(SMTPMailServerImpl.java:164) ... 129 more Caused by: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: timestamp check failed at com.sun.net.ssl.internal.ssl.Alerts.getSSLException(Alerts.java:174) at com.sun.net.ssl.internal.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1649) at com.sun.net.ssl.internal.ssl.Handshaker.fatalSE(Handshaker.java:241) at com.sun.net.ssl.internal.ssl.Handshaker.fatalSE(Handshaker.java:235) at com.sun.net.ssl.internal.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1206) at com.sun.net.ssl.internal.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:136) at com.sun.net.ssl.internal.ssl.Handshaker.processLoop(Handshaker.java:593) at com.sun.net.ssl.internal.ssl.Handshaker.process_record(Handshaker.java:529) at com.sun.net.ssl.internal.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:893) at com.sun.net.ssl.internal.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1138) at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1165) at com.sun.net.ssl.internal.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1149) at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:548) at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:485) at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1913) ... 134 more Caused by: sun.security.validator.ValidatorException: PKIX path validation failed: java.security.cert.CertPathValidatorException: timestamp check failed at sun.security.validator.PKIXValidator.doValidate(PKIXValidator.java:289) at sun.security.validator.PKIXValidator.doValidate(PKIXValidator.java:263) at sun.security.validator.PKIXValidator.engineValidate(PKIXValidator.java:184) at sun.security.validator.Validator.validate(Validator.java:218) at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.validate(X509TrustManagerImpl.java:126) at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:209) at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:249) at com.sun.net.ssl.internal.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1185) ... 144 more Caused by: java.security.cert.CertPathValidatorException: timestamp check failed at sun.security.provider.certpath.PKIXMasterCertPathValidator.validate(PKIXMasterCertPathValidator.java:139) at sun.security.provider.certpath.PKIXCertPathValidator.doValidate(PKIXCertPathValidator.java:328) at sun.security.provider.certpath.PKIXCertPathValidator.engineValidate(PKIXCertPathValidator.java:178) at java.security.cert.CertPathValidator.validate(CertPathValidator.java:250) at sun.security.validator.PKIXValidator.doValidate(PKIXValidator.java:275) ... 151 more Caused by: java.security.cert.CertificateExpiredException: NotAfter: Fri May 17 19:59:59 EDT 2013 at sun.security.x509.CertificateValidity.valid(CertificateValidity.java:256) at sun.security.x509.X509CertImpl.checkValidity(X509CertImpl.java:570) at sun.security.provider.certpath.BasicChecker.verifyTimestamp(BasicChecker.java:157) at sun.security.provider.certpath.BasicChecker.check(BasicChecker.java:109) at sun.security.provider.certpath.PKIXMasterCertPathValidator.validate(PKIXMasterCertPathValidator.java:117) ... 155 more DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc] DEBUG SMTP: useEhlo true, useAuth true DEBUG SMTP: useEhlo true, useAuth true DEBUG SMTP: trying to connect to host "copper.gehringgroup.local", port 587, isSSL false 220 copper.gehringgroup.local Microsoft ESMTP MAIL Service ready at Mon, 20 May 2013 10:10:15 -0400 DEBUG SMTP: connected to host "copper.gehringgroup.local", port: 587 EHLO emerald.mybentek.local 250-copper.gehringgroup.local Hello [10.1.2.27] 250-SIZE 104857600 250-PIPELINING 250-DSN 250-ENHANCEDSTATUSCODES 250-STARTTLS 250-AUTH GSSAPI NTLM 250-8BITMIME 250-BINARYMIME 250 CHUNKING DEBUG SMTP: Found extension "SIZE", arg "104857600" DEBUG SMTP: Found extension "PIPELINING", arg "" DEBUG SMTP: Found extension "DSN", arg "" DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg "" DEBUG SMTP: Found extension "STARTTLS", arg "" DEBUG SMTP: Found extension "AUTH", arg "GSSAPI NTLM" DEBUG SMTP: Found extension "8BITMIME", arg "" DEBUG SMTP: Found extension "BINARYMIME", arg "" DEBUG SMTP: Found extension "CHUNKING", arg "" STARTTLS 220 2.0.0 SMTP server ready
Hi,
Looking at the logs, it appears like the mail server is encrypted and requires SSL for authentication and looking at your settings, the SSL is uncheck. Try to check that option and if the problem persist, you can follow the guide on this doco to import the mail server certificate to the keystore of JIRA
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