Question : Manually testing AUTH NTLM via SMTP

Assuming I telnet to a local exchange server's SMTP port and am presented with the following:

        # telnet ourhost.domain 25
        Trying 192.168.1.100...
        Connected to ourhost.domain.
        Escape character is '^]'.
        220 ourhost.domain Microsoft ESMTP MAIL Service ready at Tue, 10 Nov 2009 15:07:14 -0800
        ehlo myhost.domain
        250-ourhost.domain Hello [192.168.1.101]
        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

How can I manually test NTLM authentication via SMTP?

Answer : Manually testing AUTH NTLM via SMTP

Not easily. You would need to create a Type 1 base-64 encoded message.

See here: http://curl.haxx.se/rfc/ntlm.html#ntlmSmtpAuthentication

I've never done this for NTLM, only for basic authentication (AUTH LOGIN) where you can provide a base64 encoded username and password for authentication.

Shaun