Jira SMTP server broken after upgrade to 6.4.12

Hi,

after upgrading from JIRA 6.4.5 to 6.4.12, our JIRA SMTP server (authenticated) in not more functioning on TLS port.

External mailserver uses public TERENA certificate.

OS is CentOS Linux release 7.2.1511 (Core) with latest updates.

java version "1.8.0_51"

Java(TM) SE Runtime Environment (build 1.8.0_51-b16)

Java HotSpot(TM) 64-Bit Server VM (build 25.51-b03, mixed mode)

 

This the full error that we receive when sending email:

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.SSLException: Received fatal alert: illegal_parameter
    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:88)
    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:727)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:303)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at org.apache.tomcat.websocket.server.WsFilter.doFilter(WsFilter.java:52)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.jira.web.filters.steps.ChainedFilterStepRunner.doFilter(ChainedFilterStepRunner.java:87)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.core.filters.HeaderSanitisingFilter.doFilter(HeaderSanitisingFilter.java:44)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:40)
    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:25)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.jira.web.filters.accesslog.AccessLogFilter.executeRequest(AccessLogFilter.java:105)
    at com.atlassian.jira.web.filters.accesslog.AccessLogFilter.doFilter(AccessLogFilter.java:89)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.jira.security.xsrf.XsrfTokenAdditionRequestFilter.doFilter(XsrfTokenAdditionRequestFilter.java:54)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.jira.web.filters.pagebuilder.PageBuilderFilter.doFilter(PageBuilderFilter.java:90)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.jira.web.filters.CommittedResponseHtmlErrorRecoveryFilter.doFilter(CommittedResponseHtmlErrorRecoveryFilter.java:63)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.seraph.filter.SecurityFilter.doFilter(SecurityFilter.java:239)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.security.auth.trustedapps.filter.TrustedApplicationsFilter.doFilter(TrustedApplicationsFilter.java:100)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.seraph.filter.BaseLoginFilter.doFilter(BaseLoginFilter.java:172)
    at com.atlassian.jira.web.filters.JiraLoginFilter.doFilter(JiraLoginFilter.java:70)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.johnson.filters.AbstractJohnsonFilter.doFilter(AbstractJohnsonFilter.java:71)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:40)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.jira.web.filters.steps.ChainedFilterStepRunner.doFilter(ChainedFilterStepRunner.java:87)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.jira.startup.JiraStartupChecklistFilter.doFilter(JiraStartupChecklistFilter.java:79)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.jira.web.filters.MultipartBoundaryCheckFilter.doFilter(MultipartBoundaryCheckFilter.java:41)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at com.atlassian.jira.web.filters.steps.ChainedFilterStepRunner.doFilter(ChainedFilterStepRunner.java:87)
    at com.atlassian.jira.web.filters.JiraFirstFilter.doFilter(JiraFirstFilter.java:61)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    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:241)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:208)
    at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:220)
    at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:122)
    at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:501)
    at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:171)
    at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:103)
    at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:116)
    at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:950)
    at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:408)
    at org.apache.coyote.http11.AbstractHttp11Processor.process(AbstractHttp11Processor.java:1070)
    at org.apache.coyote.AbstractProtocol$AbstractConnectionHandler.process(AbstractProtocol.java:611)
    at org.apache.tomcat.util.net.JIoEndpoint$SocketProcessor.run(JIoEndpoint.java:316)
    at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1142)
    at java.util.concurrent.ThreadPoolExecutor$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.MessagingException: Could not convert socket to TLS;
  nested exception is:
    javax.net.ssl.SSLException: Received fatal alert: illegal_parameter
    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.sendWithMessageId(SMTPMailServerImpl.java:173)
    ... 193 more
Caused by: javax.net.ssl.SSLException: Received fatal alert: illegal_parameter
    at sun.security.ssl.Alerts.getSSLException(Alerts.java:208)
    at sun.security.ssl.Alerts.getSSLException(Alerts.java:154)
    at sun.security.ssl.SSLSocketImpl.recvAlert(SSLSocketImpl.java:2023)
    at sun.security.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:1125)
    at sun.security.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1375)
    at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1403)
    at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1387)
    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)
    ... 198 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 "smtp.unimib.it", port 587, isSSL false
220 pablo2.pablo.unimib.it ESMTP CommuniGate Pro 6.0.8
DEBUG SMTP: connected to host "smtp.unimib.it", port: 587

EHLO helpdesk.unimib.it
250-pablo2.pablo.unimib.it we trust you helpdesk.unimib.it
250-DSN
250-SIZE 44040192
250-STARTTLS
250-AUTH LOGIN PLAIN
250-ETRN
250-TURN
250-ATRN
250-NO-SOLICITING
250-8BITMIME
250-HELP
250-PIPELINING
250 EHLO
DEBUG SMTP: Found extension "DSN", arg ""
DEBUG SMTP: Found extension "SIZE", arg "44040192"
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN"
DEBUG SMTP: Found extension "ETRN", arg ""
DEBUG SMTP: Found extension "TURN", arg ""
DEBUG SMTP: Found extension "ATRN", arg ""
DEBUG SMTP: Found extension "NO-SOLICITING", arg ""
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "HELP", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "EHLO", arg ""
STARTTLS
220 please start a TLS connection

--------------------------------------------

 

There is also a problem with a Mail Handler that looks very similar. The Handler can't connect via SSL to our IMAP server:

 

2015-12-18 12:14:00,229 atlassian-scheduler-quartz1.clustered_Worker-2 WARN anonymous    Handler per Internal [atlassian.mail.incoming.mailfetcherservice] Handler per Internal[10100]: javax.mail.MessagingException: Received fatal alert: illegal_parameter while connecting to host 'imap.unimib.it' as user 'internal-issues@unimib.it' via protocol 'imaps, caused by: javax.net.ssl.SSLException: Received fatal alert: illegal_parameter

 

Perhaps something broken with certificates in 6.4.12 version?

2 answers

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No - there's no SMTP server in JIRA, it just connects to the server you tell it to to send email.

The problem you are having here is purely to do with the SSL setup on your mail server and what Tomcat or Java (i.e. not JIRA) are doing with the certificates you have provided for them.

It's quite likely that you've run into a bug with ecliptic curves that affects Tomcat though - try adding -Dcom.sun.net.ssl.enableECC=false to the environment and restarting JIRA.  If that doesn't help, also try adding -Djsse.enableSNIExtension=false  (I had to use both when I ran into it, but try one at a time first)

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Dear Nic and Support,

first of all, I know that JIRA don't carry a SMTP server, i was simply referring to the "Outgoing Mail" configuration section, which points to "SMTP Mail Server" and is obviously "external".

 

Please note that we haven't introduced any modifications (certifcates or similar) when upgrading from 6.4.5.

 

We haave tried with your suggestion, at first enabling the configurations one at a time and then together, the problem still persisted.

 

Tried then to comment out some /opt/atlassian/jira/jre/lib/security/java.security directives, with no success.

 

Tried with the old cacerts file, problem still there.

 

In the end we have tried the last resort, fully replacing the jre directory of jra 6.4.12 with the one shipped with jira 6.4.5.

 

Now the software is working properly, so for us this is clearly a bug symptom of the Java version shipped with Jira version 6.4.12 (or something related).

 

As a reminder, these are the two Java version involved:

 

Jira 6.4.5:

 

java version "1.8.0_40"

 

Java(TM) SE Runtime Environment (build 1.8.0_40-b25)

 

Java HotSpot(TM) 64-Bit Server VM (build 25.40-b25, mixed mode)

 

Jira 6.4.12:

 

java version "1.8.0_51"

 

Java(TM) SE Runtime Environment (build 1.8.0_51-b16)

 

Java HotSpot(TM) 64-Bit Server VM (build 25.51-b03, mixed mode)

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