SMTP SASL SASL AUTH NTLM RFC4954 NTLM # Server-side AUTH NTLM REPLY AUTH 334 NTLM supported REPLY %b64[NTLMSSP%00%01%00%00%00%06%82%08%00%00%00%00%00%00%00%00%00%00%00%00%00%00%00%00%00]b64% 334 TlRMTVNTUAACAAAAAgACADAAAACGggEAc51AYVDgyNcAAAAAAAAAAG4AbgAyAAAAQ0MCAAQAQwBDAAEAEgBFAEwASQBTAEEAQgBFAFQASAAEABgAYwBjAC4AaQBjAGUAZABlAHYALgBuAHUAAwAsAGUAbABpAHMAYQBiAGUAdABoAC4AYwBjAC4AaQBjAGUAZABlAHYALgBuAHUAAAAAAA== REPLY TlRMTVNTUAADAAAAGAAYAEAAAAAYABgAWAAAAAAAAABwAAAACAAIAHAAAAALAAsAeAAAAAAAAAAAAAAAhoIBAFpkQwKRCZFMhjj0tw47wEjKHRHlvzfxQamFcheMuv8v+xeqphEO5V41xRd7R9deOXRlc3R1c2VyV09SS1NUQVRJT04= 235 Authenticated # Client-side smtp NTLM SSL !SSPI SMTP NTLM authentication mail body smtp://%HOSTIP:%SMTPPORT/%TESTNUMBER --mail-rcpt recipient@example.com --mail-from sender@example.com -u testuser:testpass -T - # Verify data after the test has been "shot" EHLO %TESTNUMBER AUTH NTLM %b64[NTLMSSP%00%01%00%00%00%06%82%08%00%00%00%00%00%00%00%00%00%00%00%00%00%00%00%00%00]b64% TlRMTVNTUAADAAAAGAAYAEAAAAAYABgAWAAAAAAAAABwAAAACAAIAHAAAAALAAsAeAAAAAAAAAAAAAAAhoIBAFpkQwKRCZFMhjj0tw47wEjKHRHlvzfxQamFcheMuv8v+xeqphEO5V41xRd7R9deOXRlc3R1c2VyV09SS1NUQVRJT04= MAIL FROM:%LTsender@example.com%GT RCPT TO:%LTrecipient@example.com%GT DATA QUIT mail body .