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[JENKINS-62585] javax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful #588

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Description

@jenkins-infra-bot

Java Version - openjdk version "1.8.0_252"
OpenJDK Runtime Environment (build 1.8.0_252-8u252-b09-1~16.04-b09)
OpenJDK 64-Bit Server VM (build 25.252-b09, mixed mode)

Mailer Plugin Version: V 1.32
Jenkins Version: 2.222.4
OS: Ubuntu

 

// code placeholder

Failed to send out e-mailjavax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful [DB6PR0301CA0028.eurprd03.prod.outlook.com]

	at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:809)
	at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:752)
	at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:669)
	at javax.mail.Service.connect(Service.java:317)
	at javax.mail.Service.connect(Service.java:176)
	at javax.mail.Service.connect(Service.java:125)
	at javax.mail.Transport.send0(Transport.java:194)
	at javax.mail.Transport.send(Transport.java:124)
	at hudson.tasks.Mailer$DescriptorImpl.doSendTestMail(Mailer.java:713)
	at java.lang.invoke.MethodHandle.invokeWithArguments(MethodHandle.java:627)
	at org.kohsuke.stapler.Function$MethodFunction.invoke(Function.java:396)
	at org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:408)
	at org.kohsuke.stapler.interceptor.RequirePOST$Processor.invoke(RequirePOST.java:77)
	at org.kohsuke.stapler.PreInvokeInterceptedFunction.invoke(PreInvokeInterceptedFunction.java:26)
	at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:212)
	at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:145)
	at org.kohsuke.stapler.MetaClass$11.doDispatch(MetaClass.java:535)
	at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:58)
	at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:747)
	at org.kohsuke.stapler.Stapler.invoke(Stapler.java:878)
	at org.kohsuke.stapler.MetaClass$4.doDispatch(MetaClass.java:280)
	at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:58)
	at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:747)
	at org.kohsuke.stapler.Stapler.invoke(Stapler.java:878)
	at org.kohsuke.stapler.Stapler.invoke(Stapler.java:676)
	at org.kohsuke.stapler.Stapler.service(Stapler.java:238)
	at javax.servlet.http.HttpServlet.service(HttpServlet.java:790)
	at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:755)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1617)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:154)
	at org.jenkinsci.plugins.ssegateway.Endpoint$SSEListenChannelFilter.doFilter(Endpoint.java:248)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at jenkins.security.ResourceDomainFilter.doFilter(ResourceDomainFilter.java:76)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at io.jenkins.blueocean.ResourceCacheControl.doFilter(ResourceCacheControl.java:134)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at io.jenkins.blueocean.auth.jwt.impl.JwtAuthenticationFilter.doFilter(JwtAuthenticationFilter.java:61)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at jenkins.telemetry.impl.UserLanguages$AcceptLanguageFilter.doFilter(UserLanguages.java:128)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:157)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:153)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:84)
	at hudson.security.UnwrapSecurityExceptionFilter.doFilter(UnwrapSecurityExceptionFilter.java:51)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at jenkins.security.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:118)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at org.acegisecurity.providers.anonymous.AnonymousProcessingFilter.doFilter(AnonymousProcessingFilter.java:125)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at org.acegisecurity.ui.rememberme.RememberMeProcessingFilter.doFilter(RememberMeProcessingFilter.java:142)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at org.acegisecurity.ui.AbstractProcessingFilter.doFilter(AbstractProcessingFilter.java:271)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at jenkins.security.BasicHeaderProcessor.doFilter(BasicHeaderProcessor.java:93)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at org.acegisecurity.context.HttpSessionContextIntegrationFilter.doFilter(HttpSessionContextIntegrationFilter.java:249)
	at hudson.security.HttpSessionContextIntegrationFilter2.doFilter(HttpSessionContextIntegrationFilter2.java:67)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:90)
	at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:171)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:49)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:82)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at org.kohsuke.stapler.DiagnosticThreadNameFilter.doFilter(DiagnosticThreadNameFilter.java:30)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at jenkins.security.SuspiciousRequestFilter.doFilter(SuspiciousRequestFilter.java:36)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:545)
	at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143)
	at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:566)
	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:1610)
	at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:233)
	at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1300)
	at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:188)
	at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:485)
	at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:1580)
	at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:186)
	at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1215)
	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:500)
	at org.eclipse.jetty.server.HttpChannel.lambda$handle$1(HttpChannel.java:383)
	at org.eclipse.jetty.server.HttpChannel.dispatch(HttpChannel.java:547)
	at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:375)
	at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:273)
	at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:311)
	at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:103)
	at org.eclipse.jetty.io.ChannelEndPoint$2.run(ChannelEndPoint.java:117)
	at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.runTask(EatWhatYouKill.java:336)
	at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.doProduce(EatWhatYouKill.java:313)
	at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.tryProduce(EatWhatYouKill.java:171)
	at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.run(EatWhatYouKill.java:129)
	at org.eclipse.jetty.util.thread.ReservedThreadExecutor$ReservedThread.run(ReservedThreadExecutor.java:375)
	at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:806)
	at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.run(QueuedThreadPool.java:938)
	at java.lang.Thread.run(Thread.java:748)

 

 

 

I tried adding below the line in 

/etc/default/jenkins

 

# Allow graphs etc. to work even when an X server is present
JAVA_ARGS="-Djava.awt.headless=true -Dmail.smtp.starttls.enable=true -Dmail.smtp.ssl.protocols=TLSv1.2"

 

 

 


Originally reported by nik0811, imported from: javax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful
  • assignee: alecharp
  • status: Open
  • priority: Critical
  • component(s): mailer-plugin
  • label(s): mailer
  • resolution: Unresolved
  • votes: 0
  • watchers: 2
  • imported: 20251211-223321
Raw content of original issue

Java Version - openjdk version "1.8.0_252" OpenJDK Runtime Environment (build 1.8.0_252-8u252-b09-1~16.04-b09) OpenJDK 64-Bit Server VM (build 25.252-b09, mixed mode)

Mailer Plugin Version: V 1.32 Jenkins Version: 2.222.4 OS: Ubuntu

 

// code placeholder

Failed to send out e-mailjavax.mail.AuthenticationFailedException: 535 5.7.3 Authentication unsuccessful [DB6PR0301CA0028.eurprd03.prod.outlook.com]

	at com.sun.mail.smtp.SMTPTransport$Authenticator.authenticate(SMTPTransport.java:809)
	at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:752)
	at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:669)
	at javax.mail.Service.connect(Service.java:317)
	at javax.mail.Service.connect(Service.java:176)
	at javax.mail.Service.connect(Service.java:125)
	at javax.mail.Transport.send0(Transport.java:194)
	at javax.mail.Transport.send(Transport.java:124)
	at hudson.tasks.Mailer$DescriptorImpl.doSendTestMail(Mailer.java:713)
	at java.lang.invoke.MethodHandle.invokeWithArguments(MethodHandle.java:627)
	at org.kohsuke.stapler.Function$MethodFunction.invoke(Function.java:396)
	at org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:408)
	at org.kohsuke.stapler.interceptor.RequirePOST$Processor.invoke(RequirePOST.java:77)
	at org.kohsuke.stapler.PreInvokeInterceptedFunction.invoke(PreInvokeInterceptedFunction.java:26)
	at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:212)
	at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:145)
	at org.kohsuke.stapler.MetaClass$11.doDispatch(MetaClass.java:535)
	at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:58)
	at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:747)
	at org.kohsuke.stapler.Stapler.invoke(Stapler.java:878)
	at org.kohsuke.stapler.MetaClass$4.doDispatch(MetaClass.java:280)
	at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:58)
	at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:747)
	at org.kohsuke.stapler.Stapler.invoke(Stapler.java:878)
	at org.kohsuke.stapler.Stapler.invoke(Stapler.java:676)
	at org.kohsuke.stapler.Stapler.service(Stapler.java:238)
	at javax.servlet.http.HttpServlet.service(HttpServlet.java:790)
	at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:755)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1617)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:154)
	at org.jenkinsci.plugins.ssegateway.Endpoint$SSEListenChannelFilter.doFilter(Endpoint.java:248)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at jenkins.security.ResourceDomainFilter.doFilter(ResourceDomainFilter.java:76)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at io.jenkins.blueocean.ResourceCacheControl.doFilter(ResourceCacheControl.java:134)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at io.jenkins.blueocean.auth.jwt.impl.JwtAuthenticationFilter.doFilter(JwtAuthenticationFilter.java:61)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at jenkins.telemetry.impl.UserLanguages$AcceptLanguageFilter.doFilter(UserLanguages.java:128)
	at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:151)
	at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:157)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:153)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:84)
	at hudson.security.UnwrapSecurityExceptionFilter.doFilter(UnwrapSecurityExceptionFilter.java:51)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at jenkins.security.ExceptionTranslationFilter.doFilter(ExceptionTranslationFilter.java:118)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at org.acegisecurity.providers.anonymous.AnonymousProcessingFilter.doFilter(AnonymousProcessingFilter.java:125)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at org.acegisecurity.ui.rememberme.RememberMeProcessingFilter.doFilter(RememberMeProcessingFilter.java:142)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at org.acegisecurity.ui.AbstractProcessingFilter.doFilter(AbstractProcessingFilter.java:271)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at jenkins.security.BasicHeaderProcessor.doFilter(BasicHeaderProcessor.java:93)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at org.acegisecurity.context.HttpSessionContextIntegrationFilter.doFilter(HttpSessionContextIntegrationFilter.java:249)
	at hudson.security.HttpSessionContextIntegrationFilter2.doFilter(HttpSessionContextIntegrationFilter2.java:67)
	at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:87)
	at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:90)
	at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:171)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:49)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:82)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at org.kohsuke.stapler.DiagnosticThreadNameFilter.doFilter(DiagnosticThreadNameFilter.java:30)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at jenkins.security.SuspiciousRequestFilter.doFilter(SuspiciousRequestFilter.java:36)
	at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1604)
	at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:545)
	at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143)
	at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:566)
	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:1610)
	at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:233)
	at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1300)
	at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:188)
	at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:485)
	at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:1580)
	at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:186)
	at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1215)
	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:500)
	at org.eclipse.jetty.server.HttpChannel.lambda$handle$1(HttpChannel.java:383)
	at org.eclipse.jetty.server.HttpChannel.dispatch(HttpChannel.java:547)
	at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:375)
	at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:273)
	at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:311)
	at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:103)
	at org.eclipse.jetty.io.ChannelEndPoint$2.run(ChannelEndPoint.java:117)
	at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.runTask(EatWhatYouKill.java:336)
	at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.doProduce(EatWhatYouKill.java:313)
	at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.tryProduce(EatWhatYouKill.java:171)
	at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.run(EatWhatYouKill.java:129)
	at org.eclipse.jetty.util.thread.ReservedThreadExecutor$ReservedThread.run(ReservedThreadExecutor.java:375)
	at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:806)
	at org.eclipse.jetty.util.thread.QueuedThreadPool$Runner.run(QueuedThreadPool.java:938)
	at java.lang.Thread.run(Thread.java:748)

 

 

 

I tried adding below the line in 

/etc/default/jenkins

 

# Allow graphs etc. to work even when an X server is present
JAVA_ARGS="-Djava.awt.headless=true -Dmail.smtp.starttls.enable=true -Dmail.smtp.ssl.protocols=TLSv1.2"

 

 

 

environment
Java Version - openjdk version &quot;1.8.0_252&quot;<br/>
OpenJDK Runtime Environment (build 1.8.0_252-8u252-b09-1~16.04-b09)<br/>
OpenJDK 64-Bit Server VM (build 25.252-b09, mixed mode)<br/>
Mailer Plugin Version: V 1.32<br/>
Jenkins Version: 2.222.4<br/>
OS: Ubuntu
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