Based on your error message, you are getting the Must issue a STARTTLS command first because in the JNDI SMTP resource configuration, mail.smtp.starttls.enable isn't turned on.
The StartTLS command is part of secure communications, but you've used a non-secure port.
See https://confluence.atlassian.com/display/JIRA/Configuring+JIRA's+SMTP+Mail+Server+to+Send+Notifications for a bit more about what the settings should be
I try to use gmail to send notification email, but it still not working, I attached the way I do with Gmail as below.
What is StartTLS on Linux and Tomcat? Cause I'm not working on Linux and Tomcat before? Can you help me in easy steps?
I just want to install a JIRA on local server that can working well as cloud. I'm very thank you.
Ok, so you've now got the correct StartTLS settings and it IS sending the right stuff. Gmail is now responding with an *Account* based failure - your previous insecure attempts have probably locked the account out as their security system would see them as an attack. As the message says, you'll need to visit gmail and log into it via a browser to confirm that you are not an attacker.
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