Problems when sending emails.
Asked by Andrei Savchenko:

Hello!  
I'm having a very annoying problem when sending emails from my standalone Confluence instalation.

It is a Confluence 4.1 version, just upgraded.  
I confirm that mail-1.4.1.jar and activation-1.0.2.jar are in the \<confluence-root\>/lib directory.  
Here is my conf/server.xml JNDI configuration:

```
&lt;Resource name="mail/RackspaceSmtpServer"          auth="Container"          type="javax.mail.Session"          mail.transport.protocol="smtp"          mail.smtp.host="secure.emailsrvr.com"          mail.smtp.port="465"          mail.smtp.auth="true"          mail.smtp.user="xxxx"          password="xxxx"          mail.smtp.starttls.enable="true"          mail.smtp.socketFactory.class="javax.net.ssl.SSLSocketFactory"          mail.debug="true"/&gt;
```

I googled, searched for the solution and nothing.  
Does anybody have a clue on how can I solve it?

Thanks!!!!

The error message I have is:

```
An error has occurred with sending the test email:java.lang.IllegalArgumentException: Mail server at location [java:comp/env/mail/RackspaceSmtpServer] is not of required type javax.mail.Session. 	at com.atlassian.mail.server.impl.SMTPMailServerImpl.getSession(SMTPMailServerImpl.java:119)	at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:169)	at com.atlassian.confluence.jmx.JmxSMTPMailServer.send(JmxSMTPMailServer.java:71)	at com.atlassian.confluence.admin.actions.mail.SendTestEmailAction.execute(SendTestEmailAction.java:52)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:168)	at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.interceptor.DefaultWorkflowInterceptor.intercept(DefaultWorkflowInterceptor.java:55)	at com.atlassian.confluence.core.ConfluenceWorkflowInterceptor.intercept(ConfluenceWorkflowInterceptor.java:37)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.xwork.interceptors.XsrfTokenInterceptor.intercept(XsrfTokenInterceptor.java:100)	at com.atlassian.confluence.xwork.ConfluenceXsrfTokenInterceptor.intercept(ConfluenceXsrfTokenInterceptor.java:25)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.security.interceptors.CaptchaInterceptor.intercept(CaptchaInterceptor.java:49)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.util.LoggingContextInterceptor.intercept(LoggingContextInterceptor.java:49)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.core.CancellingInterceptor.intercept(CancellingInterceptor.java:23)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.security.websudo.WebSudoInterceptor.intercept(WebSudoInterceptor.java:69)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.security.actions.PermissionCheckInterceptor.intercept(PermissionCheckInterceptor.java:57)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.setup.webwork.BootstrapAwareInterceptor.intercept(BootstrapAwareInterceptor.java:26)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.user.actions.UserAwareInterceptor.intercept(UserAwareInterceptor.java:58)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.pages.actions.CommentAwareInterceptor.intercept(CommentAwareInterceptor.java:50)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.pages.actions.PageAwareInterceptor.intercept(PageAwareInterceptor.java:130)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.spaces.actions.SpaceAwareInterceptor.intercept(SpaceAwareInterceptor.java:77)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.core.actions.LastModifiedInterceptor.intercept(LastModifiedInterceptor.java:38)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.core.ConfluenceAutowireInterceptor.intercept(ConfluenceAutowireInterceptor.java:49)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.xwork.interceptors.TransactionalInvocation.invokeAndHandleExceptions(TransactionalInvocation.java:76)	at com.atlassian.xwork.interceptors.TransactionalInvocation.invokeInTransaction(TransactionalInvocation.java:61)	at com.atlassian.xwork.interceptors.XWorkTransactionInterceptor.intercept(XWorkTransactionInterceptor.java:56)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.atlassian.confluence.xwork.SetupIncompleteInterceptor.intercept(SetupIncompleteInterceptor.java:43)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)	at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)	at com.opensymphony.xwork.DefaultActionProxy.execute(DefaultActionProxy.java:115)	at com.atlassian.confluence.servlet.ConfluenceServletDispatcher.serviceAction(ConfluenceServletDispatcher.java:53)	at com.opensymphony.webwork.dispatcher.ServletDispatcher.service(ServletDispatcher.java:199)	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.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:46)	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.confluence.security.websudo.MessagesDecoratorFilter.doFilter(MessagesDecoratorFilter.java:59)	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.opensymphony.sitemesh.webapp.SiteMeshFilter.obtainContent(SiteMeshFilter.java:129)	at com.opensymphony.sitemesh.webapp.SiteMeshFilter.doFilter(SiteMeshFilter.java:77)	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.confluence.jmx.JmxFilter.doFilter(JmxFilter.java:106)	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.ServletContextThreadLocalFilter.doFilter(ServletContextThreadLocalFilter.java:19)	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.confluence.util.LoggingContextFilter.doFilter(LoggingContextFilter.java:40)	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.confluence.web.filter.ThreadLocalCacheFilter.doFilter(ThreadLocalCacheFilter.java:22)	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)	at com.atlassian.confluence.util.UserThreadLocalFilter.doFilter(UserThreadLocalFilter.java:44)	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.seraph.filter.SecurityFilter.doFilter(SecurityFilter.java:211)	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 com.atlassian.confluence.util.AbstractBootstrapHotSwappingFilter.doFilter(AbstractBootstrapHotSwappingFilter.java:30)	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.seraph.filter.BaseLoginFilter.doFilter(BaseLoginFilter.java:150)	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.confluence.util.ClusterHeaderFilter.doFilter(ClusterHeaderFilter.java:37)	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:72)	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)	at org.springframework.orm.hibernate.support.OpenSessionInViewFilter.doFilterInternal(OpenSessionInViewFilter.java:170)	at com.atlassian.spring.filter.FlushingSpringSessionInViewFilter.doFilterInternal(FlushingSpringSessionInViewFilter.java:29)	at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:76)	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)	at com.atlassian.confluence.util.ConfluenceErrorFilter.doFilter(ConfluenceErrorFilter.java:22)	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 org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)	at com.atlassian.confluence.core.datetime.RequestTimeThreadLocalFilter.doFilter(RequestTimeThreadLocalFilter.java:35)	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:74)	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.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.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:46)	at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:66)	at com.atlassian.confluence.extra.webdav.servlet.filter.ReverseProxyFilter.doFilter(ReverseProxyFilter.java:427)	at com.atlassian.confluence.extra.webdav.servlet.filter.AbstractHttpFilter.doFilter(AbstractHttpFilter.java:34)	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.confluence.web.filter.validateparam.RequestParamValidationFilter.doFilter(RequestParamValidationFilter.java:58)	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.confluence.web.filter.TranslationModeFilter.doFilter(TranslationModeFilter.java:43)	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.confluence.plugin.servlet.filter.ActionContextCleanUp.doFilter(ActionContextCleanUp.java:71)	at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)	at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)	at com.atlassian.confluence.web.filter.LanguageExtractionFilter.doFilter(LanguageExtractionFilter.java:54)	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.confluence.util.RequestCacheThreadLocalFilter.doFilter(RequestCacheThreadLocalFilter.java:25)	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 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.confluence.servlet.FourOhFourErrorLoggingFilter.doFilter(FourOhFourErrorLoggingFilter.java:65)	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.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(Unknown Source)
```


Answers:
author: Javier Villalobos
body: I tested 3 ways to configure mail service and it didn't work, so i got number version of my confluence, I searched documentation for these version about mail configuration, I made exactly the doc said and it worked!


author: Sumit Khanna
body: I have never setup a JINDI name or places the JavaMail libraries in my TOMCAT_HOME/lib folder. I'm currently running Confluence off a Jelastic cloud hosting instance. I get the following exception most of the time. Occasionally the e-mail will actually get through. I'm not sure what's going on here. If I check the postfix logs, there isn't even a connection attempt. I know it's connectible because it occasionally works and I can connect to that SMTP server via telnet from other authorized addresses. I think it's a Confluence bug. I'm running 5.1.4.

An error has occurred with sending the test email:  
java.lang.NullPointerException  
at com.atlassian.confluence.admin.actions.mail.SendTestEmailAction.execute(SendTestEmailAction.java:58)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:168)  
at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.core.ConfluenceWorkflowInterceptor.intercept(ConfluenceWorkflowInterceptor.java:64)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.xwork.interceptors.XsrfTokenInterceptor.intercept(XsrfTokenInterceptor.java:100)  
at com.atlassian.confluence.xwork.ConfluenceXsrfTokenInterceptor.intercept(ConfluenceXsrfTokenInterceptor.java:26)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.security.interceptors.CaptchaInterceptor.intercept(CaptchaInterceptor.java:49)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.validation.MessageHolderInterceptor.intercept(MessageHolderInterceptor.java:42)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.util.LoggingContextInterceptor.intercept(LoggingContextInterceptor.java:49)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.core.CancellingInterceptor.intercept(CancellingInterceptor.java:23)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.xwork.HttpMethodValidationInterceptor.intercept(HttpMethodValidationInterceptor.java:72)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.security.websudo.WebSudoInterceptor.intercept(WebSudoInterceptor.java:71)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.themes.ThemeContextInterceptor.intercept(ThemeContextInterceptor.java:68)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.security.actions.PermissionCheckInterceptor.intercept(PermissionCheckInterceptor.java:57)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.setup.webwork.BootstrapAwareInterceptor.intercept(BootstrapAwareInterceptor.java:26)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.user.actions.UserAwareInterceptor.intercept(UserAwareInterceptor.java:58)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.pages.actions.CommentAwareInterceptor.intercept(CommentAwareInterceptor.java:50)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.pages.actions.PageAwareInterceptor.intercept(PageAwareInterceptor.java:151)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.spaces.actions.SpaceAwareInterceptor.intercept(SpaceAwareInterceptor.java:77)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.xwork.FlashScopeInterceptor.intercept(FlashScopeInterceptor.java:25)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.core.actions.LastModifiedInterceptor.intercept(LastModifiedInterceptor.java:31)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.core.ConfluenceAutowireInterceptor.intercept(ConfluenceAutowireInterceptor.java:49)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.xwork.interceptors.TransactionalInvocation.invokeAndHandleExceptions(TransactionalInvocation.java:76)  
at com.atlassian.xwork.interceptors.TransactionalInvocation.invokeInTransaction(TransactionalInvocation.java:61)  
at com.atlassian.xwork.interceptors.XWorkTransactionInterceptor.intercept(XWorkTransactionInterceptor.java:56)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.xwork.SetupIncompleteInterceptor.intercept(SetupIncompleteInterceptor.java:43)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.atlassian.confluence.security.interceptors.XXSSSecurityHeaderInterceptor.intercept(XXSSSecurityHeaderInterceptor.java:21)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.opensymphony.xwork.interceptor.AroundInterceptor.intercept(AroundInterceptor.java:35)  
at com.opensymphony.xwork.DefaultActionInvocation.invoke(DefaultActionInvocation.java:165)  
at com.opensymphony.xwork.DefaultActionProxy.execute(DefaultActionProxy.java:115)  
at com.atlassian.confluence.servlet.ConfluenceServletDispatcher.serviceAction(ConfluenceServletDispatcher.java:57)  
at com.opensymphony.webwork.dispatcher.ServletDispatcher.service(ServletDispatcher.java:199)  
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.confluence.web.filter.DebugFilter.doFilter(DebugFilter.java:44)  
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.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.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:66)  
at com.atlassian.mywork.client.filter.ServingRequestsFilter.doFilter(ServingRequestsFilter.java:37)  
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.prettyurls.filter.PrettyUrlsDispatcherFilter.doFilter(PrettyUrlsDispatcherFilter.java:60)  
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.prettyurls.filter.PrettyUrlsSiteMeshFilter.doFilter(PrettyUrlsSiteMeshFilter.java:70)  
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.prettyurls.filter.PrettyUrlsMatcherFilter.doFilter(PrettyUrlsMatcherFilter.java:56)  
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.confluence.security.websudo.MessagesDecoratorFilter.doFilter(MessagesDecoratorFilter.java:59)  
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.opensymphony.sitemesh.webapp.SiteMeshFilter.obtainContent(SiteMeshFilter.java:129)  
at com.opensymphony.sitemesh.webapp.SiteMeshFilter.doFilter(SiteMeshFilter.java:77)  
at com.atlassian.confluence.util.profiling.ProfilingPageFilter.doFilter(ProfilingPageFilter.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.plugin.remotable.plugin.module.permission.ApiScopingFilter.doFilter(ApiScopingFilter.java:62)  
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.prettyurls.filter.PrettyUrlsCombinedMatchDispatcherFilter.doFilter(PrettyUrlsCombinedMatchDispatcherFilter.java:61)  
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.confluence.jmx.JmxFilter.doFilter(JmxFilter.java:106)  
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.ServletContextThreadLocalFilter.doFilter(ServletContextThreadLocalFilter.java:21)  
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.confluence.util.LoggingContextFilter.doFilter(LoggingContextFilter.java:40)  
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.confluence.util.UserThreadLocalFilter.doFilter(UserThreadLocalFilter.java:41)  
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.seraph.filter.SecurityFilter.doFilter(SecurityFilter.java:211)  
at com.atlassian.confluence.web.filter.ConfluenceSecurityFilter.doFilter(ConfluenceSecurityFilter.java:28)  
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)  
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)  
at com.atlassian.confluence.web.filter.ThreadLocalCacheFilter.doFilter(ThreadLocalCacheFilter.java:22)  
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 com.atlassian.confluence.util.AbstractBootstrapHotSwappingFilter.doFilter(AbstractBootstrapHotSwappingFilter.java:30)  
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.seraph.filter.BaseLoginFilter.doFilter(BaseLoginFilter.java:150)  
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:55)  
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.prettyurls.filter.PrettyUrlsCombinedMatchDispatcherFilter.doFilter(PrettyUrlsCombinedMatchDispatcherFilter.java:61)  
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.confluence.util.ClusterHeaderFilter.doFilter(ClusterHeaderFilter.java:37)  
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:72)  
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)  
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)  
at org.springframework.orm.hibernate.support.OpenSessionInViewFilter.doFilterInternal(OpenSessionInViewFilter.java:170)  
at com.atlassian.spring.filter.FlushingSpringSessionInViewFilter.doFilterInternal(FlushingSpringSessionInViewFilter.java:29)  
at org.springframework.web.filter.OncePerRequestFilter.doFilter(OncePerRequestFilter.java:76)  
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)  
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)  
at com.atlassian.confluence.util.ConfluenceErrorFilter.doFilter(ConfluenceErrorFilter.java:22)  
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 org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)  
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)  
at com.atlassian.confluence.core.datetime.RequestTimeThreadLocalFilter.doFilter(RequestTimeThreadLocalFilter.java:35)  
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:74)  
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.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.plugin.servlet.filter.IteratingFilterChain.doFilter(IteratingFilterChain.java:46)  
at com.atlassian.plugin.servlet.filter.DelegatingPluginFilter$1.doFilter(DelegatingPluginFilter.java:66)  
at com.atlassian.plugin.remotable.plugin.module.oauth.OAuth2LOFilter.doFilter(OAuth2LOFilter.java:70)  
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.plugin.remotable.host.common.service.http.bigpipe.BigPipeRequestIdFilter.doFilter(BigPipeRequestIdFilter.java:35)  
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.prettyurls.filter.PrettyUrlsCombinedMatchDispatcherFilter.doFilter(PrettyUrlsCombinedMatchDispatcherFilter.java:61)  
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.confluence.extra.webdav.servlet.filter.ReverseProxyFilter.doFilter(ReverseProxyFilter.java:427)  
at com.atlassian.confluence.extra.webdav.servlet.filter.AbstractHttpFilter.doFilter(AbstractHttpFilter.java:34)  
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.confluence.web.filter.validateparam.RequestParamValidationFilter.doFilter(RequestParamValidationFilter.java:58)  
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.confluence.web.filter.TranslationModeFilter.doFilter(TranslationModeFilter.java:43)  
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.confluence.plugin.servlet.filter.ActionContextCleanUp.doFilter(ActionContextCleanUp.java:71)  
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)  
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)  
at com.atlassian.confluence.web.filter.LanguageExtractionFilter.doFilter(LanguageExtractionFilter.java:53)  
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.confluence.util.RequestCacheThreadLocalFilter.doFilter(RequestCacheThreadLocalFilter.java:25)  
at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:235)  
at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:206)  
at com.atlassian.confluence.web.filter.DebugFilter.doFilter(DebugFilter.java:44)  
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 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.confluence.servlet.FourOhFourErrorLoggingFilter.doFilter(FourOhFourErrorLoggingFilter.java:65)  
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:103)  
at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:615)  
at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:109)  
at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:293)  
at org.apache.coyote.http11.Http11Processor.process(Http11Processor.java:861)  
at org.apache.coyote.http11.Http11Protocol$Http11ConnectionHandler.process(Http11Protocol.java:606)  
at org.apache.tomcat.util.net.JIoEndpoint$Worker.run(JIoEndpoint.java:489)  
at java.lang.Thread.run(Thread.java:722)  


author: hsuhailah
body: > java.lang.IllegalArgumentException: Mail server at location \[java:comp/env/mail/RackspaceSmtpServer\] is not of required type javax.mail.Session

Perhaps the specificed Resource name and JNDI Location were falsed? If you replace the existing JNDI Location with this '`java:comp/env/mail/Session', `and changed the Resource name to

|-----------------------------------------|
| `<``Resource` `name``=``"mail/Session"` |

will it work? I see that the smtp port is similar to Gmail smtp port. Alternatively, you can try to[configure Gmail as the Mail Server](http://confluence.atlassian.com/display/CONF30/How+do+I+configure+Confluence+to+use+GMail+as+the+mail+server) instead.


author: Remo Siegwart
body: It looks like the files **mail-1.4.1.jar** and **activation-1.0.2.jar** you once moved to **\<confluence-root\>/lib** exist now (after the upgrade) again in the **\<confluence-root\>/confluence/WEB-INF/lib** directory. I would try to remove them and test again.

Hope this helps

comments: author: Andrei Savchenko
body: Thanks a lot, but no, still not working after deleting those files and restarting the server. It's a very misterious problem, this one.


author: Remo Siegwart
body: Strange. Found a [comment on the official documentation page of Confluence about exactly the same problem](http://confluence.atlassian.com/display/DOC/How+do+I+configure+Confluence+to+use+GMail+as+the+mail+server?focusedCommentId=218279322#comment-218279322) and it seems this worked for him. Are you using a WAR release of Confluence?


Tags: email

jndi