Java spring boot - JavaMailSender errors

Question

I am fairly new to Java spring - I am getting the following errors when trying to send a test email.

Error in sending email:

org.springframework.mail.MailSendException: Mail server connection failed; nested exception is javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 587; nested exception is: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?. Failed messages: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 587; nested exception is: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?; message exceptions (1) are: Failed message 1: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 587; nested exception is: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?"

SimepleEmailController.java

package controller;

import javax.mail.internet.MimeMessage;

import org.springframework.beans.factory.annotation.Autowired;
import org.springframework.mail.javamail.JavaMailSender;
import org.springframework.mail.javamail.MimeMessageHelper;
import org.springframework.stereotype.Controller;
import org.springframework.web.bind.annotation.RequestMapping;
import org.springframework.web.bind.annotation.ResponseBody;

@Controller
public class SimpleEmailController {

    @Autowired
    private JavaMailSender sender;

    @RequestMapping("/simpleemail")
    @ResponseBody
    String home() {
        try {
            sendEmail();
            return "Email Sent!";
        }catch(Exception ex) {
            return "Error in sending email: "+ex;
        }
    }

    private void sendEmail() throws Exception{
        MimeMessage message = sender.createMimeMessage();
        MimeMessageHelper helper = new MimeMessageHelper(message);

        helper.setTo("[email protected]");
        helper.setText("How are you?");
        helper.setSubject("Hi");

        sender.send(message);
    }
}

The application.properties settings are as follows - testing on a test account

spring.mail.port=587
spring.mail.host=smtp.gmail.com
[email protected]
spring.mail.password=zzzzzzzzzzz
spring.mail.protocol=smtp
spring.mail.defaultEncoding=UTF-8

spring.mail.properties.mail.smtp.starttls.enable=true
spring.mail.properties.mail.smtp.auth = true
spring.mail.properties.mail.smtp.socketFactory.port = 25
spring.mail.properties.mail.smtp.socketFactory.class = javax.net.ssl.SSLSocketFactory
spring.mail.properties.mail.smtp.socketFactory.fallback = true
spring.mail.properties.mail.smtp.ssl.enable=true

[email protected]

I tried a different port - 465 -- are these configurations correct etc.. -- — The Old County
Please hide your personal data from code(e.g. email login pass, host, port), because it is not secure — Vahan Mambreyan

Ajit Soman Ajit Soman · Accepted Answer · 2017-09-03T14:53:59

Remove this line from your application.properties: spring.mail.properties.mail.smtp.ssl.enable=true

Since your are using port 587 which is for sending message with TLS. You should use above configuration if you are using port 465 which is a SMTP SSL port.

Java spring boot - JavaMailSender errors

4 Answers