Just want to add here as we had a similar issue where NTLM was working in our environments and not working in client environments, we even tried Negotiate but that is failing too. We were not able to reproduce it in internal environments as our LAN Manager Authentication Level setting was different and session security was also turned off. This was all on jdk1.6.0_25. When we upgraded to jdk 1.7.0_15 everything started working (NTLM and Negotiate), we figured out that Authenticator.setDefault() was also getting called which was not the case with jdk 1.6.0_25.
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