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Trying to send email using Jenkins- using the email notification plugin, using ssl option.

Initially was getting bad id/pwd error- also got login blocked alert emails from google. So enabled the less secure apps. The error changed to javax.mail.AuthenticationFailedException: 534-5.7.14

I do not have 2-step auth enabled in gmail. Read a couple of posts here suggesting - need to use 2-step auth method with gmail - is that the way to go?

How do I install older plugin? I downloaded the older Mailer plugin 1.23 (wget) it is a .hpi file. But in my plug folder only has jpi files. What it is supposed to be? Do I just go to the console and uninstall the current plugin and just copy this hpi file to /plugins folder?

Able to install the .hpi finally Advanced installation The Update Center only allows the installation of the most recently released version of a plugin. In cases where an older release of the plugin is desired, a Jenkins administrator can download an older .hpi archive and manually install that on the Jenkins master.

From the web UI Assuming a .hpi file has been downloaded, a logged-in Jenkins administrator may upload the file from within the web UI:

Navigate to the Manage Jenkins > Manage Plugins page in the web UI.

Click on the Advanced tab.

Choose the .hpi file under the Upload Plugin section.

Upload the plugin file.

After uploading .hpi from local system using the GUI) - the Mailer plugin version shows the new older Mailer version 1.23. But you have to reconfigure it.

But still same error: javax.mail.AuthenticationFailedException: 534-5.7.14

support.google.com/mail/answer/78754 q128sm12098788pga.24 - gsmtp. checking the google support link - I think am doing everything as suggested

Sam-T
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  • Yes, two-step authentication should work. This [post](https://stackoverflow.com/a/49048152/361089) provides the relevant details. – Technext Oct 04 '19 at 13:27
  • Also read [this](https://stackoverflow.com/a/57621730/361089) answer in case you're using latest version of `Mailer` plugin. You might need to downgrade it. – Technext Oct 04 '19 at 13:35
  • How do install older plugin - check comments on main post. – Sam-T Oct 07 '19 at 15:15
  • [This](https://stackoverflow.com/a/19588907/361089) answer tells you how to install plugin using GUI. As far as extension name is concerned, both should work. `.jpi` is the newer extension name that Jenkins uses. – Technext Oct 07 '19 at 15:41
  • I did update the plugin to 2.63. But still get same error : javax.mail.AuthenticationFailedException: 534-5.7.14 Please 534-5.7.14 log in via your web browser and then try again. 534-5.7.14 Learn more at 534 5.7.14 https://support.google.com/mail/answer/78754 q128sm12098788pga.24 - gsmtp. checking the google support link - I am doing everything as suggested. – Sam-T Oct 07 '19 at 15:46
  • I still have "allow less secure apps login". But one difference I noticed now is - when I did not have this on earlier - I was getting "blocked" alerts from Google, they had stopped when I enabled. But now once again I am getting blocked alerts from google. – Sam-T Oct 07 '19 at 15:58
  • Tried using yahoo smtp it came up with its own error: javax.mail.AuthenticationFailedException: 535 5.7.0 (#AUTH005) Too many bad auth attempts. This is totally wheird. Did not get any security alerts in yahoo – Sam-T Oct 07 '19 at 16:18
  • What version of `Mailer` plugin do you have? The link i suggested in my second comment recommends to downgrade `Mailer` plugin to version `1.23`. – Technext Oct 07 '19 at 16:19
  • I have Mailer plugin 1.23 now. With Google smtp I get javax.mail.AuthenticationFailedException: 534-5.7.14 – Sam-T Oct 07 '19 at 17:15
  • I tried this with **outlook smtp** also - got errors: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection? com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [MWHPR02CA0014.namprd02.prod.o – Sam-T Oct 09 '19 at 21:49

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