I was unable to configure Hudson to use the google smtp server to send
notification emails.

I get this error:

ERROR: 530 5.7.0 Must issue a STARTTLS command first. c44sm12222795hsc.12

com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS
command first.

at com.sun.mail.smtp.SMTPTransport.issueSendCommand
(SMTPTransport.java:1388)
at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:959)
at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:583)
at javax.mail.Transport.send0(Transport.java:169)
at javax.mail.Transport.send(Transport.java:98)
at hudson.tasks.MailSender.execute(MailSender.java:75)
at hudson.tasks.Mailer._perform(Mailer.java:77)
at hudson.tasks.Mailer.perform(Mailer.java:71)
at hudson.tasks.BuildStepCompatibilityLayer.perform
(BuildStepCompatibilityLayer.java:33)
at hudson.model.AbstractBuild$AbstractRunner.performAllBuildStep
(AbstractBuild.java:318)
at hudson.model.AbstractBuild$AbstractRunner.performAllBuildStep
(AbstractBuild.java:306)
at hudson.model.Build$RunnerImpl.post2(Build.java:126)
at hudson.model.AbstractBuild$AbstractRunner.post
(AbstractBuild.java:291)
at hudson.model.Run.run(Run.java:813)
at hudson.model.Build.run(Build.java:88)
at hudson.model.ResourceController.execute(ResourceController.java:70)
at hudson.model.Executor.run(Executor.java:88)

This can be fixed on the java mail api setting this property:

props.put("mail.smtp.starttls.enable","true");

Enabling SSL did not work either. It would be nice if the Hudson mail
configuration UI allowed us to configure this.

Thanks
Matias G. Rodriguez