JAVAMAIL : AUTH NTLM failed

Question

i try to send email with java in local network,using microsoft exchange server

there is my code :

import java.io.UnsupportedEncodingException;
import java.util.Properties;

import javax.mail.Message;
import javax.mail.MessagingException;
import javax.mail.PasswordAuthentication;
import javax.mail.Session;
import javax.mail.Transport;
import javax.mail.internet.AddressException;
import javax.mail.internet.InternetAddress;
import javax.mail.internet.MimeMessage;


public class Main {


        public static void main(String[] args) {

            final String username = "username@MyDomain.com";
            final String password = "password";

            Properties props = new Properties();
            props.put("mail.smtp.auth", "true");
            props.put("mail.debug", "true");
            props.put("mail.smtp.host", "exchange_host.MyDomain.com");
            props.put("mail.smtp.port", "25");
            props.put("mail.smtp.auth.mechanisms","NTLM");
            props.put("mail.smtp.auth.ntlm.domain","MyDomain");


            Session session = Session.getInstance(props,new MyAuthenticator(username,password));

            try {

                Message message = new MimeMessage(session);
                message.setFrom(new InternetAddress("from_adress@MyDomain.com"));
                message.setRecipients(Message.RecipientType.TO,
                    InternetAddress.parse("recipent_adresse"));
                message.setSubject("Testing Subject");
                message.setText("Dear Mail Crawler,"
                    + "\n\n No spam to my email, please!");

                Transport.send(message);

                System.out.println("Done");

            } catch (MessagingException e) {
                throw new RuntimeException(e);
            }
        }
    }

and this is my authentificator class :

import javax.mail.Authenticator;
import javax.mail.PasswordAuthentication;

public class MyAuthenticator extends Authenticator {

     String user;
     String pw;
     public MyAuthenticator (String username, String password)
     {
        super();
        this.user = username;
        this.pw = password;
     }
    public PasswordAuthentication getPasswordAuthentication()
    {
       return new PasswordAuthentication(user, pw);
    }

}

i use the NTLM mechanism but i get this error :

DEBUG: JavaMail version 1.4.7
DEBUG: successfully loaded resource: /META-INF/javamail.default.providers
DEBUG: Tables of loaded providers
DEBUG: Providers Listed By Class Name: {com.sun.mail.smtp.SMTPSSLTransport=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Oracle], com.sun.mail.smtp.SMTPTransport=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle], com.sun.mail.imap.IMAPSSLStore=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Oracle], com.sun.mail.pop3.POP3SSLStore=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Oracle], com.sun.mail.imap.IMAPStore=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Oracle], com.sun.mail.pop3.POP3Store=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Oracle]}
DEBUG: Providers Listed By Protocol: {imaps=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Oracle], imap=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Oracle], smtps=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Oracle], pop3=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Oracle], pop3s=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Oracle], smtp=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]}
DEBUG: successfully loaded resource: /META-INF/javamail.default.address.map
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "echange_server.MyDomain.com", port 25, isSSL false
220 echange_server.MyDomain.com Microsoft ESMTP MAIL Service ready at Mon, 30 Sep 2013 09:01:08 +0100
DEBUG SMTP: connected to host "echange_server.MyDomain.com", port: 25

EHLO host.MyDomain.com
250-echange_server.MyDomain.com Hello [xx.xx.xx.xx]
250-SIZE
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-X-ANONYMOUSTLS
250-AUTH NTLM
250-X-EXPS GSSAPI NTLM
250-8BITMIME
250-BINARYMIME
250-CHUNKING
250-XEXCH50
250-XRDST
250 XSHADOW
DEBUG SMTP: Found extension "SIZE", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "DSN", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "X-ANONYMOUSTLS", arg ""
DEBUG SMTP: Found extension "AUTH", arg "NTLM"
DEBUG SMTP: Found extension "X-EXPS", arg "GSSAPI NTLM"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "BINARYMIME", arg ""
DEBUG SMTP: Found extension "CHUNKING", arg ""
DEBUG SMTP: Found extension "XEXCH50", arg ""
DEBUG SMTP: Found extension "XRDST", arg ""
DEBUG SMTP: Found extension "XSHADOW", arg ""
DEBUG SMTP: Attempt to authenticate using mechanisms: NTLM
DEBUG SMTP: AUTH NTLM failed

Exception in thread "main" java.lang.RuntimeException: javax.mail.AuthenticationFailedException: 250-exchange_host.MyDomain.com Hello [xx.xx.xx.xx]

    at testPakcage.Main.main(Main.java:51)
Caused by: javax.mail.AuthenticationFailedException: 250-exchange_host.MyDomain.com Hello [xx.xx.xx.xx]

please help me,i past several day to search solution but i found nothing

Answer 1

I have this working connecting to our Exchange 2010 server via NTLM.

NTLM uses your Windows login and password for authentication rather than your email address and password.

I made the following changes:

1) Username should be Windows login, NOT email address. NTLM uses your Windows credentials for authentication.

2) mail.smtp.auth.ntlm.domain should be your windows domain - i.e. the part before the slash if you normally log on to your Windows machine with "MYDOMAIN\id12345" as username.

Updated code below:

public class Main {
  public static void main(String[] args) {

    // *** CHANGED ***
    final String username = "id12345"; // ID you log into Windows with
    final String password = "MyWindowsPassword";

    Properties props = new Properties();
    props.put("mail.smtp.auth", "true");
    props.put("mail.debug", "true");

    props.put("mail.smtp.host", "exchangeserver.mydomain.com");
    props.put("mail.smtp.port", "25");
    props.put("mail.smtp.auth.mechanisms","NTLM");

    // *** CHANGED ***
    props.put("mail.smtp.auth.ntlm.domain","WINDOMAIN"); // Domain you log into Windows with


    Session session = Session.getInstance(props,new MyAuthenticator(username,password));

    try {

        Message message = new MimeMessage(session);
        message.setFrom(new InternetAddress("john.smith@mydomain.com"));
        message.setRecipients(Message.RecipientType.TO,
                InternetAddress.parse("the.recipient@mydomain.com"));
        message.setSubject("Test email");
        message.setText("TEST EMAIL");

        Transport.send(message);

        System.out.println("Done");

    } catch (MessagingException e) {
        e.printStackTrace();
    }
  }


  public static class MyAuthenticator extends Authenticator {

    String user;
    String pw;
    public MyAuthenticator (String username, String password)
    {
        super();
        this.user = username;
        this.pw = password;
    }
    public PasswordAuthentication getPasswordAuthentication()
    {
        return new PasswordAuthentication(user, pw);
    }
  }
}

For what it's worth, your original post helped me solve the problems I have had connecting which have been going on for several days.

One final point, you probably need to disable / change antivirus settings to allow access out on port 25.

Answer 2

I had the same problem and after finding out that javamail does not support NTLMv2 authentication, I worked out a workaround that requires JCIFS library though.

I downloded the javamail api source code (https://java.net/projects/javamail/pages/Home) and edited the class com.sun.mail.auth.Ntlm to add the missing support for NTLMv2 using the JCIFS library support (http://jcifs.samba.org).

The first modification in file Ntlm.java was in method init0, and consisted of adding the missing flag NTLMSSP_NEGOTIATE_NTLM2:

private void init0() {
// ANDREA LUCIANO:
//    turn on the NTLMv2 negotiation flag in TYPE1 messages: 
//    NTLMSSP_NEGOTIATE_NTLM2   (0x00080000) 
//  See also http://davenport.sourceforge.net/ntlm.html#type1MessageExample

    type1 = new byte[256];
    type3 = new byte[256];
    System.arraycopy(new byte[] {'N','T','L','M','S','S','P',0,1}, 0,
            type1, 0, 9);
    type1[12] = (byte) 3;
    type1[13] = (byte) 0xb2;
    type1[14] = (byte) 0x08;  // ANDREA LUCIANO - added

... }

The second modification was to replace the method generateType3Msg with this:

public String generateType3Msg(String challenge) {
    /* First decode the type2 message */
    byte[] type2 = null;
    try {
       type2 = BASE64DecoderStream.decode(challenge.getBytes("us-ascii"));
       logger.fine("type 2 message: " + toHex(type2)); // ANDREA LUCIANO - added
    } catch (UnsupportedEncodingException ex) {
       // should never happen
       assert false;
    }
    jcifs.ntlmssp.Type2Message t2m;
    try {
          t2m = new jcifs.ntlmssp.Type2Message(type2);
    } catch (IOException ex) {
          logger.log(Level.FINE, "Invalid Type 2 message", ex);
          return "";   // will fail later
    }

    final int type2Flags = t2m.getFlags();
    final int type3Flags = type2Flags & (0xffffffff ^ (jcifs.ntlmssp.NtlmFlags.NTLMSSP_TARGET_TYPE_DOMAIN | jcifs.ntlmssp.NtlmFlags.NTLMSSP_TARGET_TYPE_SERVER));

    jcifs.ntlmssp.Type3Message t3m = new jcifs.ntlmssp.Type3Message(t2m, password, ntdomain, username, hostname, type3Flags);
       return jcifs.util.Base64.encode(t3m.toByteArray());
}

The simpest way I found to patch the library is to compile the class and update the library jar file:

"c:\Program Files\Java\jdk1.5.0_22\bin\javac.exe" -cp jcifs-1.3.17.jar;javax.mail-1.5.2.jar -d . Ntlm.java 
 jar uvf javax.mail-1.5.2.jar com\sun\mail\auth\Ntlm.class

To enable debug as much as possible, I used the following code in the main method of my test class:

    final InputStream inputStream = Main.class.getResourceAsStream("/logging.properties");
    LogManager.getLogManager().readConfiguration(inputStream);

    Properties props = new Properties();

    props.put("mail.debug", "true");
    props.put("mail.debug.auth", "true");

with this logging.properties:

   # Logging
   handlers = java.util.logging.ConsoleHandler

  .level = INFO

  # Console Logging
  java.util.logging.ConsoleHandler.level = INFO

Before applying the patch the test was stuck after sending Type 1 message, because my Exchange server required NTLMv2 authentication. After the patch the athentication was done successfully.