Java mail sender quit just after 354 status

Question

I am trying to use JavaMailSenderImpl to send mail. Below is the program and output showing no error, but still not sending mail.

Mail Configuration:

@Configuration 
public class MailConfig {

    @Autowired
    private Environment env;

    @Bean
    public JavaMailSender javaMailService() {

        JavaMailSenderImpl mailSender = new JavaMailSenderImpl();

        mailSender.setHost(env.getProperty("spring.mail.host"));
        mailSender.setUsername(env.getProperty("spring.mail.username"));
        mailSender.setPassword(env.getProperty("spring.mail.password"));

        Properties javaMailProperties = new Properties();
        javaMailProperties.put("mail.smtp.ssl.enable", "true");
        javaMailProperties.put("mail.smtp.starttls.enable", "false");
        javaMailProperties.put("mail.smtp.auth", "true");
        javaMailProperties.put("mail.transport.protocol", "smtp");
        javaMailProperties.put("mail.debug", "true");
        javaMailProperties.put("mail.smtp.ssl.checkserveridentity", "true");
        javaMailProperties.put("mail.smtp.socketFactory.port", "465");

        mailSender.setJavaMailProperties(javaMailProperties);

        return mailSender;
    }
}

    @GetMapping("/user/resetPassword/{email}")
    public GenericResponse resetPassword(HttpServletRequest request, 
      @PathVariable("email") String userEmail) throws UserNotFoundException {
        User user = userRepository.findByEmail(userEmail);
        if (user == null) {
            throw new UserNotFoundException("USER NOT FOUND");
        }
        try {
        String token = UUID.randomUUID().toString();
        createPasswordResetTokenForUser(user, token);
        mailSender.send(constructResetTokenEmail("http://localhost:7005", token, user));
        }
        catch(Exception ex) {
            ex.printStackTrace();
        }
        return new GenericResponse("message.resetPasswordEmail");
    }

    public void createPasswordResetTokenForUser(User user, String token) {
        PasswordResetToken myToken = new PasswordResetToken(token, user);

        passwordTokenRepository.save(myToken);
    }

    private SimpleMailMessage constructResetTokenEmail(
              String contextPath, String token, User user) {
                String url = contextPath + "/user/changePassword?token=" + token;
                String message = "message.resetPassword";
                return constructEmail("Reset Password", message + " \r\n" + url, user);
    }

    private SimpleMailMessage constructEmail(String subject, String body,
            User user) {
        SimpleMailMessage email = new SimpleMailMessage();
        email.setSubject(subject);
        email.setText(body);
        email.setTo("[email protected]");
        email.setFrom("[email protected]");
        return email;
    }

}

Here is the output of the code:

DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "AUTH", arg "LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH"
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "CHUNKING", arg ""
DEBUG SMTP: Found extension "SMTPUTF8", arg ""
DEBUG SMTP: Attempt to authenticate using mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM XOAUTH2 
DEBUG SMTP: Using mechanism LOGIN
DEBUG SMTP: AUTH LOGIN command trace suppressed
DEBUG SMTP: AUTH LOGIN succeeded
DEBUG SMTP: use8bit false
MAIL FROM:<[email protected]>
250 2.1.0 OK u5sm8797330pfu.198 - gsmtp
RCPT TO:<[email protected]>
250 2.1.5 OK u5sm8797330pfu.198 - gsmtp
DEBUG SMTP: Verified Addresses
DEBUG SMTP:   [email protected]
DATA
354  Go ahead u5sm8797330pfu.198 - gsmtp
QUIT

Answer 1

Experiencing the same issue I tried to find out what happened to fix the issue.

the full bug :

While dialing with SMTP server, after RCPT TO command, javax.mail send DATA. The server answers 354 + custom message.

It seems that on some platform (linux was the only one impacted on the software I develop) with some specific messages (the failing one had double quotes inside) the javax.mail lib just send QUIT.

As the server is waiting for the mail followed by :

.

the server just waits for other content and never answers. javax.mail fails with a timeout.

the root cause

This was a dependency convergence issue :

• we use javax.mail-api 1.6.2
• we use apache-commons.commons-mail 1.5
  • apache-commons.commons-mail depends on javax.mail-api 1.5.6 (even if compatible with 1.6.2)

The fix

We needed 1.6.2 due to some feature in embeds.

The solution was to exclude transitive dependency and explicitely include com.sun.mail:javax.mail at version 1.6.2.