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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("set-your-recipient-email-here@gmail.com");
        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
spring.mail.username=xxxxxxxxxxxxx@gmail.com
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

support.mail.address=xxxxxxxxxxxxxxx@gmail.com
The Old County
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4 Answers4

1

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.

Ajit Soman
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  • Error in sending email: org.springframework.mail.MailAuthenticationException: Authentication failed; nested exception is javax.mail.AuthenticationFailedException: 534-5.7.14 Please log in via your web browser and 534-5.7.14 then try again. 534-5.7.14 Learn more at 534 5.7.14 https://support.google.com/mail/answer/78754 17sm825599ljp.80 - gsmtp -- with port 465 – The Old County Sep 03 '17 at 17:33
  • 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; – The Old County Sep 03 '17 at 17:35
  • - no still fail -- Error in sending email: org.springframework.mail.MailAuthenticationException: Authentication failed; nested exception is javax.mail.AuthenticationFailedException: 534-5.7.14 Please log in via your web browser and 534-5.7.14 then try again. 534-5.7.14 Learn more at 534 5.7.14 https://support.google.com/mail/answer/78754 100sm393966lfs.45 - gsmtp – The Old County Sep 03 '17 at 17:42
0

Try to use your @ as setTo() param for a first quick test. Then, you can let default configuration, you don't need much of it.

spring.mail.host=smtp.gmail.com
spring.mail.username=romanineers@gmail.com
spring.mail.password=****** #hope it wasn't your real password :)
spring.mail.properties.mail.smtp.auth = true
Montassar El Béhi
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  • so take out a bulk of properties? – The Old County Sep 03 '17 at 14:37
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    protocol will be auto detected, ports have conventional default values, so yes, works fine for me.. – Montassar El Béhi Sep 03 '17 at 14:44
  • failed --- Error in sending email: org.springframework.mail.MailSendException: Failed messages: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. b75sm830640lff.61 - gsmtp ; message exceptions (1) are: Failed message 1: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. b75sm830640lff.61 - gsmtp – The Old County Sep 03 '17 at 17:38
0

As per the error you are getting, just set spring.mail.properties.mail.smtp.ssl.enable=true property value to false and try.

Amardeep
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0

Problem fixed --- javax.mail.AuthenticationFailedException is thrown while sending email in java -- have to configure the gmail to allow less secure apps -- 

spring.mail.port=465
spring.mail.host=smtp.gmail.com
spring.mail.username=xx@gmail.com
spring.mail.password=yyyyy
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 = 465
spring.mail.properties.mail.smtp.socketFactory.class = javax.net.ssl.SSLSocketFactory
spring.mail.properties.mail.smtp.socketFactory.fallback = false
spring.mail.properties.mail.smtp.ssl.enable=false

support.mail.address=xx@gmail.com
The Old County
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