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Trying to configure Jenkins to send emails after builds. Had a previous issue with gmail authentication; the good folk on Stack Exchange helped be get the 'Test email recipient' in System Configuration working.

https://stackoverflow.com/questions/57794536/configure-jenkins-to-send-gmail-what-am-i-missing

After I implemented suggestions from the community I got Jenkins to send emails on bad builds and 'Jenkins build is back to normal...'

However when I tried today I am still ble to send 'test email recipient' successfully but I'm getting this in my logs when I try to build:

C:\Program Files (x86)\Jenkins\workspace\listEnvironmentVariables>exit 9009 
Build step 'Execute Windows batch command' marked build as failure
Sending e-mails to: [email protected]
ERROR: 530-5.5.1 Authentication Required. Learn more at
530 5.5.1  https://support.google.com/mail/?p=WantAuthError t6sm2844926oij.39 - gsmtp

com.sun.mail.smtp.SMTPSendFailedException: 530-5.5.1 Authentication Required. Learn more at
530 5.5.1  https://support.google.com/mail/?p=WantAuthError t6sm2844926oij.39 - gsmtp

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2057)
    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1580)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1097)
    at javax.mail.Transport.send0(Transport.java:195)
    at javax.mail.Transport.send(Transport.java:124)
    at hudson.tasks.MailSender.run(MailSender.java:130)
    at hudson.tasks.Mailer.perform(Mailer.java:175)

This worked yesterday and aside from rebooting my machine I didn't intentionally make any changes.

Windows 10, latest Jenkins version, latest Mailer plugin, 2-step auth for Gmail, stopped VPN service... at my wits end here!

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  • ave you figured it out? Having the same issue..
    – vilkg
    Commented Feb 10, 2020 at 17:19
  • Nope - and I gave up awhile ago A bit surprised no one chimed in with an answer. I posted other Jenkins-related questions and the community was super awesome and helpful!
    – Lou
    Commented Feb 16, 2020 at 15:55
  • For me, upgrading Jenkins plugins fixed the issue. No idea what was wrong :)
    – vilkg
    Commented Feb 20, 2020 at 13:45
  • vilkg - I'll give that a try and post back. Thanks
    – Lou
    Commented Feb 21, 2020 at 14:24

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