Jenkins cant send mail

Question

I am working with an instance of Jenkins set up by someone other than myself (who is no longer available for questions) and it is unable to send mail, when I do a test email (or if a job tries to send email) I get the following error which I have looked around and found little to no mention of on the internet:

com.sun.mail.smtp.SMTPAddressFailedException: 453 4.7.1 <[e-mail]>: Sender address rejected: You are not authorized to send as [e-mail]

    at com.sun.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:1733)
Caused: javax.mail.SendFailedException: Invalid Addresses;
nested exception is:
    com.sun.mail.smtp.SMTPAddressFailedException: 453 4.7.1 <[e-mail]>: Sender address rejected: You are not authorized to send as [e-mail]

at com.sun.mail.smtp.SMTPTransport.rcptTo(SMTPTransport.java:1835)
at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1098)
at javax.mail.Transport.send0(Transport.java:195)
at javax.mail.Transport.send(Transport.java:124)
at hudson.tasks.Mailer$DescriptorImpl.doSendTestMail(Mailer.java:585)
at java.lang.invoke.MethodHandle.invokeWithArguments(MethodHandle.java:627)
at org.kohsuke.stapler.Function$MethodFunction.invoke(Function.java:343)
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:184)
at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:117)
at org.kohsuke.stapler.MetaClass$1.doDispatch(MetaClass.java:129)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:58)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:715)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:845)
at org.kohsuke.stapler.MetaClass$5.doDispatch(MetaClass.java:248)
at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:58)
at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:715)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:845)
at org.kohsuke.stapler.Stapler.invoke(Stapler.java:649)
at org.kohsuke.stapler.Stapler.service(Stapler.java:238)
at javax.servlet.http.HttpServlet.service(HttpServlet.java:790)
at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:841)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1650)
at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:154)
at hudson.plugins.greenballs.GreenBallFilter.doFilter(GreenBallFilter.java:59)
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:1637)
at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:99)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1637)
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:1637)
at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:49)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1637)
at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:82)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1637)
at org.kohsuke.stapler.DiagnosticThreadNameFilter.doFilter(DiagnosticThreadNameFilter.java:30)
at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1637)
at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:533)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:143)
at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:524)
at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:132)
at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:190)
at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:1595)
at org.eclipse.jetty.server.handler.ScopedHandler.nextHandle(ScopedHandler.java:188)
at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1253)
at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:168)
at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:473)
at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:1564)
at org.eclipse.jetty.server.handler.ScopedHandler.nextScope(ScopedHandler.java:166)
at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1155)
at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:141)
at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:132)
at org.eclipse.jetty.server.Server.handle(Server.java:564)
at org.eclipse.jetty.server.HttpChannel.handle(HttpChannel.java:317)
at org.eclipse.jetty.server.HttpConnection.onFillable(HttpConnection.java:251)
at org.eclipse.jetty.io.AbstractConnection$ReadCallback.succeeded(AbstractConnection.java:279)
at org.eclipse.jetty.io.FillInterest.fillable(FillInterest.java:110)
at org.eclipse.jetty.io.ChannelEndPoint$2.run(ChannelEndPoint.java:124)
at org.eclipse.jetty.util.thread.Invocable.invokePreferred(Invocable.java:128)
at org.eclipse.jetty.util.thread.Invocable$InvocableExecutor.invoke(Invocable.java:222)
at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.doProduce(EatWhatYouKill.java:294)
at org.eclipse.jetty.util.thread.strategy.EatWhatYouKill.run(EatWhatYouKill.java:199)
at winstone.BoundedExecutorService$1.run(BoundedExecutorService.java:77)
at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1142)
at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:617)
at java.lang.Thread.run(Thread.java:805)

Answer 1

Looks like the problem is server side. The important part of that errors is:

Sender address rejected: You are not authorized to send as [e-mail]

This happens when I try to send mail as a secondary account instead of my primary account. It means you need to be logged in to the mail server as the user from whom you want to send mail. I do not get this error when I am sending from an account that doesn't really exist, only real accounts that require authentication. Check with your mail admin to see what is required to send mail from that account. They can either give you credentials or allow permissions for others to send as.