Confluence is not authenticating to email server

I've recently deployed the atlassian suite of apps, including jira, bamboo, stash, etc.

Mail is being sent via a smtps server on port 465, though I've tested confluence on port 25 as well.

JIRA uses the same configuration options and can send/authenticate/secure pop mail from the server on the ssmtp and pops ports.

When attempting to connect to port 465/ssmtp, confluence times out. When I try port 25, no authentication is sent to the mail server and (appropriately) the mail server refuses to relay.

Below is the error output I receive from confluence:

An error has occurred with sending the test email:

com.atlassian.mail.MailException: javax.mail.SendFailedException: Invalid Addresses;

nested exception is:

com.sun.mail.smtp.SMTPAddressFailedException: 554 5.7.1 <james@jameskyle.org>: Relay access denied

at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:191)

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.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: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.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:150)

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.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:52)

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.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: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.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: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.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.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: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)

Caused by: javax.mail.SendFailedException: Invalid Addresses;

nested exception is:

com.sun.mail.smtp.SMTPAddressFailedException: 554 5.7.1 <james@jameskyle.org>: Relay access denied

at com.sun.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:1294)

at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:635)

at javax.mail.Transport.send0(Transport.java:189)

at javax.mail.Transport.send(Transport.java:118)

at alt.javax.mail.TransportImpl.send(TransportImpl.java:18)

at com.atlassian.mail.server.impl.SMTPMailServerImpl.send(SMTPMailServerImpl.java:177)

... 216 more

Caused by: com.sun.mail.smtp.SMTPAddressFailedException: 554 5.7.1 <james@jameskyle.org>: Relay access denied

at com.sun.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:1192)

... 221 more

3 answers

1 accepted

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Confluence doesn't support e-mail authentication prior Confluece v 5.0.

That's another unbelievable limitation, you will discover more and more if use Confluence heavily.

Upgraded to 5.x. Everything works as expected now.

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This isnt an authentication problem its an authorization problem, ie its nothing you can fix in Confluence. Your Mailserver administrator has deined relaying of outbound mail (this is quite common to avoid spamming). Approach your admin, and ask that your confluence server/user be allowed to relay.

I'm the mail administrator. I've blocked non-authenticated relaying of outbound mail. I should also note the working Jira is on the same host as the non-working confluence. Here's the mail logs from both:

Working Jira:

Oct 26 08:45:50 tfoundry postfix/smtpd[15714]: connect from unknown[75.29.211.5]
Oct 26 08:45:50 tfoundry postfix/smtpd[15714]: Anonymous TLS connection established from unknown[75.29.211.5]: TLSv1 with cipher RC4-MD5 (128/128 bits)
Oct 26 08:45:51 tfoundry postfix/smtpd[15714]: 3B33C1A006D: client=unknown[75.29.211.5], sasl_method=PLAIN, sasl_username=admin
Oct 26 08:45:51 tfoundry postfix/cleanup[15717]: 3B33C1A006D: message-id=&lt;753591337.3.1351266350443.JavaMail.jira@support.mydomain.com&gt;
Oct 26 08:45:51 tfoundry postfix/qmgr[12815]: 3B33C1A006D: from=&lt;info@support.mydomain.com&gt;, size=870, nrcpt=1 (queue active)
Oct 26 08:45:51 tfoundry postfix/smtpd[15714]: disconnect from unknown[75.29.211.5]
Oct 26 08:45:51 tfoundry postfix/smtp[15718]: connect to ASPMX.L.GOOGLE.COM[2607:f8b0:400e:c01::1b]:25: Network is unreachable
Oct 26 08:45:52 tfoundry postfix/smtp[15718]: 3B33C1A006D: to=&lt;me@otherdomain.com&gt;, relay=ASPMX.L.GOOGLE.COM[173.194.79.26]:25, delay=1.6, delays=0.22/0.02/0.49/0.88, dsn=2.0.0, status=sent (250 2.0.0 OK 1351266352 pe8si2941706pbc.40)
Oct 26 08:45:52 tfoundry postfix/qmgr[12815]: 3B33C1A006D: removed

Not working confluence (from same host)

Oct 26 08:50:42 tfoundry postfix/smtpd[15733]: connect from unknown[75.29.211.5]
Oct 26 08:50:42 tfoundry postfix/smtpd[15733]: NOQUEUE: reject: RCPT from unknown[75.29.211.5]: 554 5.7.1 &lt;me@otherdomain.com&gt;: Relay access denied; from=&lt;info@confluence.mydomain.com&gt; to=&lt;me@otherdomain.com&gt; proto=ESMTP helo=&lt;support.mydomain.com&gt;
Oct 26 08:50:42 tfoundry postfix/smtpd[15733]: disconnect from unknown[75.29.211.5]

In the first case with Jira, a TLS connection is established and the sender authenticates. In the second, Confluence does not attempt to authenticate and so the relay is rejected.

Well, so if relay access is denied due to lack of authentication, I would guess you dont have creds set for outbound mail in confluence.

https://confluence.atlassian.com/display/DOC/Configuring+a+Server+for+Outgoing+Mail

Contrast outbound mail server details for JIRA vs Confluence?

A failure of Confluence to authenticate with an smtp server would be a gaping bug?

The authentication values are set, copy pasted the same as the JIRA ones. Weird huh?

Also, note, it's not attempting to authenticate and failing...it never attempts to authenticate at all

Use a mail client, eg thunderbird etc, connect with JIRA creds, be happy that works, replace with Confluence creds. If that doesnt work, its not confluence, its your server config thats not right.

I am currently successfully connected to the mail server with these apps:

- Mail.app on my desktop, port 465 secure smtp

- Jira (on same host as confluence)

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If you can't connect by Secure SMTP, you may not have your JAVA cacerts file updated with the CA trust chain of your Secure (SSL?) SMTP server, try using the SSLPoke test (here) I contributed a long time ago to validate that you Java runtime is correctly configured, assuming you can get your Confluence Java Runtime to be active in your path prior to testing).

If you are not able to connect via :25 at all, my money says its due to mail server configuration. Is your desktop client able to connect on :25 or generate the same result?

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