How to send mail via outlook using spring boot?

Question

My application.properties file contains following configuration :-

spring.mail.properties.mail.smtp.connecttimeout=5000
  spring.mail.properties.mail.smtp.timeout=3000
  spring.mail.properties.mail.smtp.writetimeout=5000
  spring.mail.host=smtp.office365.com
  spring.mail.password=password
  spring.mail.port=587
  [email protected]
  spring.mail.properties.mail.smtp.starttls.enable=true
  security.require-ssl=true
  spring.mail.properties.mail.smpt.auth=true

Java classes for implemting the mail servers are :

@Component
public class SmtpMailSender {
@Autowired
private JavaMailSender javaMailSender;

public void sendMail(String to, String subject, String body) throws MessagingException {
    MimeMessage message = javaMailSender.createMimeMessage();
    MimeMessageHelper helper;
    helper = new MimeMessageHelper(message, true);//true indicates multipart message
    helper.setSubject(subject);
    helper.setTo(to);
    helper.setText(body, true);//true indicates body is html
    javaMailSender.send(message);
}
}

My controller class is :

@RestController
public class MailController {

@Autowired
SmtpMailSender smtpMailSender;

@RequestMapping(path = "/api/mail/send")
public void sendMail() throws MessagingException {
    smtpMailSender.sendMail("[email protected]", "testmail", "hello!");
}
}

when I send get request (/api/mail/send) following error occurs:

{
"timestamp": 1496815958863,
"status": 500,
"error": "Internal Server Error",
"exception": "org.springframework.mail.MailAuthenticationException",
"message": "Authentication failed; nested exception is 
javax.mail.AuthenticationFailedException: ;\n  nested exception 
is:\n\tjavax.mail.MessagingException: Exception reading response;\n  nested 
exception is:\n\tjava.net.SocketTimeoutException: Read timed out",
"path": "/api/mail/send"
}

Any help would be heartily appreciated.

Answer 1

You must specify the sender using setFrom method to perform authentication on outlook.com:

@Component
public class SmtpMailSender {

    @Value("${spring.mail.username}")
    private String from;

    @Autowired
    private JavaMailSender javaMailSender;

    public void sendMail(String to, String subject, String body) throws MessagingException {
        MimeMessage message = javaMailSender.createMimeMessage();
        MimeMessageHelper helper;
        helper = new MimeMessageHelper(message, true);//true indicates multipart message

        helper.setFrom(from) // <--- THIS IS IMPORTANT

        helper.setSubject(subject);
        helper.setTo(to);
        helper.setText(body, true);//true indicates body is html
        javaMailSender.send(message);
    }
}

outlook.com checks that you're not trying to pretend you're somebody else.