Issue
You were using an SMTP server to send email notifications from the CloudBees CD server, but after upgrading to version 10.0+ the send operation is failing with an error similar to the one shown below:
EmailNotificationFailure: Unable to send email. Authentication failed; nested exception is javax.mail.AuthenticationFailedException: No authentication mechansims supported by both server and client
Environment
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CloudBees CD (CloudBees Flow) Server > 10.0.1
Resolution
According to the product release notes, there were some changes affecting the email settings. As you can see in the link below:
Now, the settings enforce TLSv.1.2 by default:
smtpSSLProtocols: Comma-separated list of protocols that are enabled for SSL connections to the SMTP server. Used to set mail.smtp.ssl.protocols system property. Default is TLSv1.2.
The poblem that you are experiencing is probably related to the fact that your SMTP server is not using TLSv1.2. So you have two options to solve this issue:
a) You enable TLSv1.2 in your SMTP server.
b) You set the smtpSSLProtocols property to a value such as: TLSv1.0,TLSv1.1,TLSv1.2 this way your server will be able to accept these requests.