Issue

I have configured Microsoft Exchange as SMTP Server for Jenkins and a similar stacktrace on my job console output is being shown

javax.mail.AuthenticationFailedException: No authentication mechansims supported by both server and client 
at com.sun.mail.smtp.SMTPTransport.authenticate(SMTPTransport.java:756) 
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:669) 
at javax.mail.Service.connect(Service.java:317) 
at javax.mail.Service.connect(Service.java:176) 
at javax.mail.Service.connect(Service.java:125) 
at javax.mail.Transport.send0(Transport.java:194) 
at javax.mail.Transport.send(Transport.java:124) 
at hudson.tasks.Mailer$DescriptorImpl.doSendTestMail(Mailer.java:566) 
...

Environment

CloudBees Jenkins Enterprise - Managed controller (CJE-MM)
CloudBees Jenkins Enterprise - Operations Center (CJE-OC)
CloudBees Jenkins Team (CJT)
CloudBees Jenkins Platform - Client controller (CJP-CM)
CloudBees Jenkins Platform - Operations Center (CJP-OC)
Jenkins LTS
Microsoft Exchange - configured as NTLM authentication.

Resolution

On Jenkins side

Add the Java Property -Dmail.smtp.auth.ntlm.domain=<Domain_name> and restart Jenkins
Configure SMTP Server under Manage Jenkins > Configure System as follows:

2.1. Use one of the following syntaxes for your user: Domain_name\username, username@Domain_name.com
2.2. Enable SSL