Unsupported or unrecognized SSL message

Question

I am trying to send emails from outlook email in Java+ springboot.

below are the configuration:

@Service
public class EmailService {

    
    String  from_address = "no-reply@jpmorganchase.com",
            password = "somepassword!sd#",
            host = "smtp.office365.com",
            port = "587",
            to_address = "no-reply@jpmorganchase.com",
            mail_subject = "Test",
            mail_content = "testing mail",
             username="",
            user_password="";
    
    
     public void sendmail(UserBean user,String uname, String pword)
        {
            username=uname;
            user_password=pword;
            to_address= user.getEmail();
            Properties props = new Properties();
            props.put("mail.smtp.user", from_address);
            props.put("mail.smtp.host", host);
            props.put("mail.smtp.port", port);
            props.put("mail.smtp.starttls.enable","true");
            props.put("mail.smtp.auth", "true");
            props.put("mail.smtp.debug", "true");
            props.put("mail.smtp.socketFactory.port", port);
            props.put("mail.smtp.socketFactory.class", "javax.net.ssl.SSLSocketFactory");
            props.put("mail.smtp.socketFactory.fallback", "false");
            mail_content = 
                     "Hello "+user.getName()+"\n"
                            +"Experience "+user.getExperience()+"\n"
                            + "Email "+user.getEmail()+"\n"
                            + "Set allocated: "+user.getSet()+"\n"
                            +"Mobile number "+user.getPhone()+"\n"+"\n"
                            + "Your login credentials are: "+"\n"
                            +"User Name: "+username+"\n"
                            +"Password:  " + user_password+"\n"+"\n"
                            + "Click on link to take test   "+"https://www.jpmorganchase.com/en_sg"+"\n" 
                            +  "Message from jpmorganchase"+user.getMessage()+"\n";
                    
            mail_subject = "jpmorganchase Online Assesment Test";
            SecurityManager security = System.getSecurityManager();

            try
            {
                Authenticator auth = new SMTPAuthenticator();
                Session session = Session.getInstance(props, auth);
                session.setDebug(true);
                MimeMessage msg = new MimeMessage(session);
                msg.setText(mail_content);
                msg.setSubject(mail_subject);
                msg.setFrom(new InternetAddress(from_address));
                msg.addRecipient(Message.RecipientType.TO, new InternetAddress(to_address));
                Transport.send(msg);
            }
            catch (Exception mex)
            {
                mex.printStackTrace();
            } 
        }
     
     public void sendConfirmationMail(User user, String confirmationToken)
        {
            Properties props = new Properties();
            props.put("mail.smtp.user", from_address);
            props.put("mail.smtp.host", host);
            props.put("mail.smtp.port", port);
            props.put("mail.smtp.starttls.enable","true");
            props.put("mail.smtp.ssl.enable","true");
            props.put("mail.smtp.auth", "true");
            props.put("mail.smtp.debug", "true");
            props.put("mail.smtp.socketFactory.port", port);
            props.put("mail.smtp.socketFactory.class", "javax.net.ssl.SSLSocketFactory");
            props.put("mail.smtp.socketFactory.fallback", "false");
            mail_content = 
                     "Hello "+user.getName()+"\n"
                     +"To confirm your account, please click here : "
                        +"http://localhost:8080/jpmorganchase/confirm-account?token="+confirmationToken;
            mail_subject="Complete Registration!";
           // String mail[] = user.getEmail().split("@");
            //to_address = mail[0]+"@gmail.com";
            to_address = user.getEmail();
                            
            SecurityManager security = System.getSecurityManager();

            try
            {
                Authenticator auth = new SMTPAuthenticator();
                Session session = Session.getInstance(props, auth);
                session.setDebug(true);
                MimeMessage msg = new MimeMessage(session);
                msg.setText(mail_content);
                msg.setSubject(mail_subject);
                msg.setFrom(new InternetAddress(from_address));
                msg.addRecipient(Message.RecipientType.TO, new InternetAddress(to_address));
                Transport.send(msg);
            }
            catch (Exception mex)
            {
                mex.printStackTrace();
            } 
        }

}

I am getting the below exception:

DEBUG: setDebug: JavaMail version 1.5.6
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: need username and password for authentication
DEBUG SMTP: protocolConnect returning false, host=smtp.office365.com, user=no-reply@jpmorganchase.com,
password=<null>
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.office365.com", port 587, isSSL false
javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 587;
  nested exception is:
  javax.net.ssl.SSLException: Unsupported or unrecognized SSL message
  at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:2120)
  at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:712)

Have tried various solutions over internet but no luck.

It is possible that SSL is not enabled in the server. If you are sure that SSL is enabled, then enable ssl debugging java.net.debug. That should give you further clue to debug. — user1929880, Mar 24 '21 at 14:30

score 2 · Accepted Answer · answered May 31 '22 at 10:22

I've spent the last 2 weeks solving this problem and searching all around. Finally, I managed to put it all together and make it work. I found key part of solution here.

In short, you need to create `SMTPTransport` instead of the classic `Transport`:

SMTPTransport t = (SMTPTransport)session.getTransport("smtp");
Socket socket = new Socket(host, port);
t.connect(socket);
t.sendMessage(message, message.getAllRecipients());

NOTE:

You do not need more than these properties:

properties.setProperty("mail.smtp.host", host);
properties.put("mail.smtp.port", port);
properties.put("mail.smtp.starttls.enable", "true");
properties.put("mail.smtp.ssl.enable", "true");

and this is essential if you are using self-signed certificates

properties.put("mail.smtp.ssl.trust", host);

If you plan to use `smtps`, after creating `Session` you need to add following:

Session session = Session.getInstance(properties, null);
...
session.setProtocolForAddress("rfc822", "smtps");

and make sure when creating SMTPTransport to get smtps like:

SMTPTransport t = (SMTPTransport)session.getTransport("smtps");

and all properties need to be defined for smtps protocol:

when using smtps properties are set as mail.smtps.<prop>

in general, based on any protocol: mail.<protocol>.<prop>

properties.setProperty("mail.smtps.host", host);
properties.put("mail.smtps.port", port);
properties.put("mail.smtps.starttls.enable", "true");
properties.put("mail.smtps.ssl.enable", "true");
properties.put("mail.smtps.ssl.trust", host);

score 0 · Answer 2 · answered Mar 13 '23 at 07:02

0

host=smtp.office365.com
port=587

I commented

properties.put("mail.smtp.ssl.enable", "true");

when use smtp.office365.com => then it work

answered Mar 13 '23 at 07:02

Nguyễn Dương

225
2
5

Unsupported or unrecognized SSL message

2 Answers2

In short, you need to create SMTPTransport instead of the classic Transport:

NOTE:

If you plan to use smtps, after creating Session you need to add following:

In short, you need to create `SMTPTransport` instead of the classic `Transport`:

If you plan to use `smtps`, after creating `Session` you need to add following: