java - Javamail NTLM Authentication Failure

Question

Trying to connect to Exchange server using NTLM in JavaMail. I can connect to SMTP, but not IMAP. I can also authenticate via the OS X Mail.app application using the identical host/username/password, account type = "IMAP", Port 143, ssl=false, authentication=NTLM, Domain Name="".

The connecting code:

import javax.mail.Session;
import javax.mail.Transport;
import javax.mail.Store;
import java.util.Properties;

    public class NTLMTest {
        public static void main(String[] args) throws Exception {
            final String host = "example.com";
            final String user = "bob";
            final String password = "password";

            final Properties properties = new Properties();
            Session session = Session.getDefaultInstance(properties);
            session.setDebug(true);

            // SMTP CONNECT
            final Transport transport = session.getTransport("smtp");
            transport.connect(host, user, password);
            System.out.println("SMTP Connect successful");

            // IMAP CONNECT
            final Store store = session.getStore("imap");
            store.connect(host, user, password);
            System.out.println("IMAP Connect Successful");

        }
    }

The output:

DEBUG: setDebug: JavaMail version 1.4.3
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]
DEBUG SMTP: useEhlo true, useAuth false
DEBUG SMTP: trying to connect to host "example.com", port 25, isSSL false
220 server18.example.com ESMTP Sendmail 8.14.3/8.14.3/Debian-5+lenny1; Thu, 2 Dec 2010 18:05:30 +0100; (No UCE/UBE) logging access from: xxx.xxx.xxx.xxx
DEBUG SMTP: connected to host "example.com", port: 25

EHLO 192.168.1.107
250-server18.example.com Hello c-xxxx [xxx.xxx.xxx.xxx], pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-8BITMIME
250-SIZE 20971520
250-DSN
250-ETRN
250-AUTH DIGEST-MD5 CRAM-MD5 LOGIN PLAIN
250-STARTTLS
250-DELIVERBY
250 HELP
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
DEBUG SMTP: Found extension "PIPELINING", arg ""
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "SIZE", arg "20971520"
DEBUG SMTP: Found extension "DSN", arg ""
DEBUG SMTP: Found extension "ETRN", arg ""
DEBUG SMTP: Found extension "AUTH", arg "DIGEST-MD5 CRAM-MD5 LOGIN PLAIN"
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "DELIVERBY", arg ""
DEBUG SMTP: Found extension "HELP", arg ""
DEBUG SMTP: Attempt to authenticate
DEBUG SMTP: check mechanisms: LOGIN PLAIN DIGEST-MD5 NTLM 
AUTH LOGIN
334 VXNlcm5hbWU6
YWR2aWVzZW5raWVzMDU=
334 UGFzc3dvcmQ6
ZGlja2hvbmluZw==
235 2.0.0 OK Authenticated
SMTP Connect successful
DEBUG: getProvider() returning javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Sun Microsystems, Inc]
DEBUG: mail.imap.fetchsize: 16384
DEBUG: mail.imap.statuscachetimeout: 1000
DEBUG: mail.imap.appendbuffersize: -1
DEBUG: mail.imap.minidletime: 10
DEBUG: trying to connect to host "example.com", port 143, isSSL false
* OK server18.example.com Cyrus IMAP4 v2.1.18-IPv6-Debian-2.1.18-5.1 server ready
A0 CAPABILITY
* CAPABILITY IMAP4 IMAP4rev1 ACL QUOTA LITERAL+ MAILBOX-REFERRALS NAMESPACE UIDPLUS ID NO_ATOMIC_RENAME UNSELECT CHILDREN MULTIAPPEND SORT THREAD=ORDEREDSUBJECT THREAD=REFERENCES IDLE AUTH=DIGEST-MD5 AUTH=NTLM AUTH=CRAM-MD5 ANNOTATEMORE
A0 OK Completed
IMAP DEBUG: AUTH: DIGEST-MD5
IMAP DEBUG: AUTH: NTLM
IMAP DEBUG: AUTH: CRAM-MD5
DEBUG: protocolConnect login, host=example.com, user=bob, password=<non-null>
DEBUG NTLM: type 1 message: Type1Message[suppliedDomain=,suppliedWorkstation=192.168.1.107,flags=0x00000201]
DEBUG NTLM: type 1 message length: 45
A1 AUTHENTICATE NTLM
+ 
TlRMTVNTUAABAAAAASIAAAAAAAAAAAAADQANACAAAAAxOTIuMTY4LjEuMTA3
+ TlRMTVNTUAACAAAAAAAAADAAAAABIgAApdhJrA6NzmwAAAAAAAAAAAAAAAAAAAAA
TlRMTVNTUAADAAAAGAAYAEAAAAAwADAAWAAAAAAAAAAAAAAAHAAcAIgAAAAaABoApAAAAAAAAAAAAAAAAQIAALV6mIutJKdZSH4IZGmvNqNFxJafzInd0yJDR4J3oe3LyBls0Y75UuwBAQAAAAAAANAS9yNDkssBVbH5v087iUIAAAAAAAAAAGEAZAB2AGkAZQBzAGUAbgBrAGkAZQBzADAANQAxADkAMgAuADEANgA4AC4AMQAuADEAMAA3AA==
A1 NO authentication failure
Exception in thread "main" javax.mail.AuthenticationFailedException: authentication failure
    at com.sun.mail.imap.IMAPStore.protocolConnect(IMAPStore.java:613)
    at javax.mail.Service.connect(Service.java:291)
    at javax.mail.Service.connect(Service.java:172)
    at com.prosc.emailplugin.NTLMTest.main(NTLMTest.java:25)
Disconnected from the target VM, address: '127.0.0.1:56125', transport: 'socket'

Process finished with exit code 1

I tried wrapping the username with backslashes, per http://www.oracle.com/technetwork/java/faq-135477.html#Exchange-login I get the following error:

Exception in thread "main" javax.mail.AuthenticationFailedException: One time use of a plaintext password will enable requested mechanism for user

Backslashes around the username in the SMTP connect portion cause it to fail. I can't tell if the "One time use" error is a step in the right direction or not.

Answer 1

I have noticed that - via SMTP - the NTLM Authentication did not work with an older version of javax.mail (up to 1.4.1) but it now works with version 1.4.5. And the user name to be specified was of the form "domainusername". Could be that same effect (difference in versions of javax.mail) would also apply to IMAP.