Jenkins Email Configuration- error "AuthenticationFailedException"

Question

I've installed my jenkins on AWS ec2 Instance and using private subnet and both the port configured in security group of the instance. I'm getting the same error for both cases- port - 465 ssl checked or port 587 ssl unchecked and I'm typing in my password correctly but I still run into this AuthenticaionFailedException.

The settings I used are:

SMTP SERVER: smtp.gmail.com 
Default user e-mail suffix: @gmail.com
USERNAME: username@gmail.com 
PASSWORD: password
USE SSL: checked/unchecked
PORT: 465/587
Reply-to-address: 
Charset: UTF-8

Error I'm getting-

javax.mail.AuthenticationFailedException: 535-5.7.8 Username and 
Password not accepted. Learn more a 535 5.7.8  
https://support.google.com/mail/?p=BadCredentials 
q13sm22788500pfn.150 - gsmtp

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:672)
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$4.doDispatch(MetaClass.java:280)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:58)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:747)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:878)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:676)
at org.kohsuke.stapler.Stapler.service(Stapler.java:238)
at javax.servlet.http.HttpServlet.service(HttpServlet.java:790)
at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:873)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1623)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:154)
at jenkins.telemetry.impl.UserLanguages$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:1610)
at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:64)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1610)
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:117)
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:1610)
at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:49)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1610)
at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:82)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1610)
at org.kohsuke.stapler.DiagnosticThreadNameFilter.doFilter(DiagnosticThreadNameFilter.java:30)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1610)
at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:540)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:146)
at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:524)
at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:132)
at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:257)
at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:1701)
at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:255)
at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1345)
at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:203)
at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:480)
at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:1668)
at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:201)
at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1247)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:144)
at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:132)
at org.eclipse.jetty.server.Server.handle(Server.java:502)
at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:370)
at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:267)
at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:305)
at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:103)
at org.eclipse.jetty.io.ChannelEndPoint$2.run(ChannelEndPoint.java:117)
at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.runTask(EatWhatYouKill.java:333)
at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.doProduce(EatWhatYouKill.java:310)
at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.tryProduce(EatWhatYouKill.java:168)
at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.run(EatWhatYouKill.java:126)
at org.eclipse.jetty.util.thread.ReservedThreadExecutor$ReservedThread.run(ReservedThreadExecutor.java:366)
at org.eclipse.jetty.util.thread.QueuedThreadPool.runJob(QueuedThreadPool.java:765)
at org.eclipse.jetty.util.thread.QueuedThreadPool$2.run(QueuedThreadPool.java:683)
at java.lang.Thread.run(Thread.java:748)

Note: I'm new to jenkins, aws so please try to put each and every steps so that I can able to understand and resolve this issue. Thanks in advance.

Answer 1

These settings worked fine for me

Implement Three things with given SMTP settings

1. Disable two factor authentication: https://myaccount.google.com/security
2. Allow less secure apps : https://www.google.com/settings/security/lesssecureapps
3. Allow new devices using the link: https://g.co/allowaccess

SMTP Settings:

• smtp.gmail.com
• Port: 465
• Use SSL
• From Email Address
• Gmail Username
• Gmail Password
• Recipient Email Address