Jira email stopped working

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

1 answer

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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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