smtp + ssl 

 
Test e-mail recipient  exception:
 
 
 
com.sun.mail.smtp.SMTPSendFailedException: 500 Error: bad syntax

at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2358)
at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1823)
at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1300)
at javax.mail.Transport.send0(Transport.java:255)
at javax.mail.Transport.send(Transport.java:124)
at hudson.tasks.Mailer$DescriptorImpl.doSendTestMail(Mailer.java:728)
at java.lang.invoke.MethodHandle.invokeWithArguments(MethodHandle.java:627)
at org.kohsuke.stapler.Function$MethodFunction.invoke(Function.java:397)
at org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:409)
at org.kohsuke.stapler.interceptor.RequirePOST$Processor.invoke(RequirePOST.java:78)
at org.kohsuke.stapler.PreInvokeInterceptedFunction.invoke(PreInvokeInterceptedFunction.java:26)
at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:207)
at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:140)
at org.kohsuke.stapler.MetaClass$11.doDispatch(MetaClass.java:558)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:59)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:766)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:898)
at org.kohsuke.stapler.MetaClass$4.doDispatch(MetaClass.java:289)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:59)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:766)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:898)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:694)
at org.kohsuke.stapler.Stapler.service(Stapler.java:240)
at javax.servlet.http.HttpServlet.service(HttpServlet.java:790)
at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:799)
at org.eclipse.jetty.servlet.ServletHandler$ChainEnd.doFilter(ServletHandler.java:1631)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:157)
at jenkins.telemetry.impl.UserLanguages$AcceptLanguageFilter.doFilter(UserLanguages.java:129)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:154)
at jenkins.security.ResourceDomainFilter.doFilter(ResourceDomainFilter.java:81)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:154)
at jenkins.metrics.impl.MetricsFilter.doFilter(MetricsFilter.java:125)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:154)
at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:160)
at org.eclipse.jetty.servlet.FilterHolder.doFilter(FilterHolder.java:193)
at org.eclipse.jetty.servlet.ServletHandler$Chain.doFilter(ServletHandler.java:1601)
at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:154)
at org.eclipse.jetty.servlet.FilterHolder.doFilter(FilterHolder.java:193)
at org.eclipse.jetty.servlet.ServletHandler$Chain.doFilter(ServletHandler.java:1601)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:94)
at jenkins.security.AcegiSecurityExceptionFilter.doFilter(AcegiSecurityExceptionFilter.java:52)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:99)
at hudson.security.UnwrapSecurityExceptionFilter.doFilter(UnwrapSecurityExceptionFilter.java:54)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:99)
at org.springframework.security.web.access.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:122)
at org.springframework.security.web.access.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:116)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:99)
at org.springframework.security.web.authentication.AnonymousAuthenticationFilter.doFilter(AnonymousAuthenticationFilter.java:109)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:99)
at org.springframework.security.web.authentication.rememberme.RememberMeAuthenticationFilter.doFilter(RememberMeAuthenticationFilter.java:102)
at org.springframework.security.web.authentication.rememberme.RememberMeAuthenticationFilter.doFilter(RememberMeAuthenticationFilter.java:93)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:99)
at org.springframework.security.web.authentication.AbstractAuthenticationProcessingFilter.doFilter(AbstractAuthenticationProcessingFilter.java:219)
at org.springframework.security.web.authentication.AbstractAuthenticationProcessingFilter.doFilter(AbstractAuthenticationProcessingFilter.java:213)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:99)
at jenkins.security.BasicHeaderProcessor.doFilter(BasicHeaderProcessor.java:97)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:99)
at org.springframework.security.web.context.SecurityContextPersistenceFilter.doFilter(SecurityContextPersistenceFilter.java:110)
at org.springframework.security.web.context.SecurityContextPersistenceFilter.doFilter(SecurityContextPersistenceFilter.java:80)
at hudson.security.HttpSessionContextIntegrationFilter2.doFilter(HttpSessionContextIntegrationFilter2.java:63)
at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:99)
at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:111)
at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:172)
at org.eclipse.jetty.servlet.FilterHolder.doFilter(FilterHolder.java:193)
at org.eclipse.jetty.servlet.ServletHandler$Chain.doFilter(ServletHandler.java:1601)
at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:53)
at org.eclipse.jetty.servlet.FilterHolder.doFilter(FilterHolder.java:193)
at org.eclipse.jetty.servlet.ServletHandler$Chain.doFilter(ServletHandler.java:1601)
at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:86)
at org.eclipse.jetty.servlet.FilterHolder.doFilter(FilterHolder.java:193)
at org.eclipse.jetty.servlet.ServletHandler$Chain.doFilter(ServletHandler.java:1601)
at org.kohsuke.stapler.DiagnosticThreadNameFilter.doFilter(DiagnosticThreadNameFilter.java:30)
at org.eclipse.jetty.servlet.FilterHolder.doFilter(FilterHolder.java:193)
at org.eclipse.jetty.servlet.ServletHandler$Chain.doFilter(ServletHandler.java:1601)
at jenkins.security.SuspiciousRequestFilter.doFilter(SuspiciousRequestFilter.java:38)
at org.eclipse.jetty.servlet.FilterHolder.doFilter(FilterHolder.java:193)
at org.eclipse.jetty.servlet.ServletHandler$Chain.doFilter(ServletHandler.java:1601)
at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:548)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143)
at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:571)
at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:127)
at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:235)
at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:1624)
at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:233)
at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1440)
at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:188)
at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:501)
at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:1594)
at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:186)
at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1355)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:141)
at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:127)
at org.eclipse.jetty.server.Server.handle(Server.java:516)
at org.eclipse.jetty.server.HttpChannel.lambda$handle$1(HttpChannel.java:487)
at org.eclipse.jetty.server.HttpChannel.dispatch(HttpChannel.java:732)
at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:479)
at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:277)
at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:311)
at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:105)
at org.eclipse.jetty.io.ChannelEndPoint$1.run(ChannelEndPoint.java:104)
at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:883)
at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.run(QueuedThreadPool.java:1034)
at java.lang.Thread.run(Thread.java:748)