SMTP NTLM Domain Extraction - Metasploit


This page contains detailed information about how to use the auxiliary/scanner/smtp/smtp_ntlm_domain metasploit module. For list of all metasploit modules, visit the Metasploit Module Library.

Table Of Contents
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Module Overview

Name: SMTP NTLM Domain Extraction
Module: auxiliary/scanner/smtp/smtp_ntlm_domain
Source code: modules/auxiliary/scanner/smtp/smtp_ntlm_domain.rb
Disclosure date: -
Last modification time: 2017-07-24 06:26:21 +0000
Supported architecture(s): -
Supported platform(s): -
Target service / protocol: smtp, smtps
Target network port(s): 25, 465, 587, 2525, 25000, 25025
List of CVEs: -

Extract the Windows domain name from an SMTP NTLM challenge.

Module Ranking and Traits

Module Ranking:

  • normal: The exploit is otherwise reliable, but depends on a specific version and can't (or doesn't) reliably autodetect. More information about ranking can be found here.

Basic Usage

This module is a scanner module, and is capable of testing against multiple hosts.

msf > use auxiliary/scanner/smtp/smtp_ntlm_domain
msf auxiliary(smtp_ntlm_domain) > show options
    ... show and set options ...
msf auxiliary(smtp_ntlm_domain) > set RHOSTS ip-range
msf auxiliary(smtp_ntlm_domain) > exploit

Other examples of setting the RHOSTS option:

Example 1:

msf auxiliary(smtp_ntlm_domain) > set RHOSTS 192.168.1.3-192.168.1.200

Example 2:

msf auxiliary(smtp_ntlm_domain) > set RHOSTS 192.168.1.1/24

Example 3:

msf auxiliary(smtp_ntlm_domain) > set RHOSTS file:/tmp/ip_list.txt

Required Options

  • RHOSTS: The target host(s), range CIDR identifier, or hosts file with syntax 'file:<path>'

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Msfconsole Usage

Here is how the scanner/smtp/smtp_ntlm_domain auxiliary module looks in the msfconsole:

msf6 > use auxiliary/scanner/smtp/smtp_ntlm_domain

msf6 auxiliary(scanner/smtp/smtp_ntlm_domain) > show info

       Name: SMTP NTLM Domain Extraction
     Module: auxiliary/scanner/smtp/smtp_ntlm_domain
    License: Metasploit Framework License (BSD)
       Rank: Normal

Provided by:
  Rich Whitcroft <[email protected]>

Check supported:
  No

Basic options:
  Name         Current Setting  Required  Description
  ----         ---------------  --------  -----------
  EHLO_DOMAIN  localhost        yes       The domain to send with the EHLO command
  RHOSTS                        yes       The target host(s), range CIDR identifier, or hosts file with syntax 'file:<path>'
  RPORT        25               yes       The target port (TCP)
  THREADS      1                yes       The number of concurrent threads (max one per host)

Description:
  Extract the Windows domain name from an SMTP NTLM challenge.

References:
  http://msdn.microsoft.com/en-us/library/cc246870.aspx

Module Options

This is a complete list of options available in the scanner/smtp/smtp_ntlm_domain auxiliary module:

msf6 auxiliary(scanner/smtp/smtp_ntlm_domain) > show options

Module options (auxiliary/scanner/smtp/smtp_ntlm_domain):

   Name         Current Setting  Required  Description
   ----         ---------------  --------  -----------
   EHLO_DOMAIN  localhost        yes       The domain to send with the EHLO command
   RHOSTS                        yes       The target host(s), range CIDR identifier, or hosts file with syntax 'file:<path>'
   RPORT        25               yes       The target port (TCP)
   THREADS      1                yes       The number of concurrent threads (max one per host)

Advanced Options

Here is a complete list of advanced options supported by the scanner/smtp/smtp_ntlm_domain auxiliary module:

msf6 auxiliary(scanner/smtp/smtp_ntlm_domain) > show advanced

Module advanced options (auxiliary/scanner/smtp/smtp_ntlm_domain):

   Name                 Current Setting  Required  Description
   ----                 ---------------  --------  -----------
   CHOST                                 no        The local client address
   CPORT                                 no        The local client port
   ConnectTimeout       10               yes       Maximum number of seconds to establish a TCP connection
   Proxies                               no        A proxy chain of format type:host:port[,type:host:port][...]
   SSL                  false            no        Negotiate SSL/TLS for outgoing connections
   SSLCipher                             no        String for SSL cipher - "DHE-RSA-AES256-SHA" or "ADH"
   SSLVerifyMode        PEER             no        SSL verification method (Accepted: CLIENT_ONCE, FAIL_IF_NO_PEER_CERT, NONE, PEER)
   SSLVersion           Auto             yes       Specify the version of SSL/TLS to be used (Auto, TLS and SSL23 are auto-negotiate) (Accepted: Auto, TLS, SSL23, SSL3, TLS1, TLS1.1, TLS1.2)
   ShowProgress         true             yes       Display progress messages during a scan
   ShowProgressPercent  10               yes       The interval in percent that progress should be shown
   VERBOSE              false            no        Enable detailed status messages
   WORKSPACE                             no        Specify the workspace for this module

Auxiliary Actions

This is a list of all auxiliary actions that the scanner/smtp/smtp_ntlm_domain module can do:

msf6 auxiliary(scanner/smtp/smtp_ntlm_domain) > show actions

Auxiliary actions:

   Name  Description
   ----  -----------

Evasion Options

Here is the full list of possible evasion options supported by the scanner/smtp/smtp_ntlm_domain auxiliary module in order to evade defenses (e.g. Antivirus, EDR, Firewall, NIDS etc.):

msf6 auxiliary(scanner/smtp/smtp_ntlm_domain) > show evasion

Module evasion options:

   Name                Current Setting  Required  Description
   ----                ---------------  --------  -----------
   TCP::max_send_size  0                no        Maxiumum tcp segment size.  (0 = disable)
   TCP::send_delay     0                no        Delays inserted before every send.  (0 = disable)

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Error Messages

This module may fail with the following error messages:

Error Messages

Check for the possible causes from the code snippets below found in the module source code. This can often times help in identifying the root cause of the problem.

<RHOST>:<RPORT> No banner received, aborting...

Here is a relevant code snippet related to the "<RHOST>:<RPORT> No banner received, aborting..." error message:

30:	    begin
31:	      domain = nil
32:	      connect
33:	
34:	      unless banner
35:	        vprint_error("#{rhost}:#{rport} No banner received, aborting...")
36:	        return
37:	      end
38:	
39:	      vprint_status("#{rhost}:#{rport} Connected: #{banner.strip.inspect}")
40:

<RHOST>:<RPORT> No NTLM extensions found

Here is a relevant code snippet related to the "<RHOST>:<RPORT> No NTLM extensions found" error message:

45:	      sock.puts("EHLO " + datastore['EHLO_DOMAIN'] + "\r\n")
46:	
47:	      # Find all NTLM references in the EHLO response
48:	      exts = sock.get_once.to_s.split(/\n/).grep(/NTLM/)
49:	      if exts.length == 0
50:	        vprint_error("#{rhost}:#{rport} No NTLM extensions found")
51:	        return
52:	      end
53:	
54:	      exts.each do |ext|
55:

<RHOST>:<RPORT> Invalid challenge response, aborting...

Here is a relevant code snippet related to the "<RHOST>:<RPORT> Invalid challenge response, aborting..." error message:

85:	
86:	          begin
87:	            # Extract the domain out of the NTLM response
88:	            ntlm_reply = Rex::Proto::NTLM::Message.parse(Rex::Text.decode_base64(challenge))
89:	            if ! ntlm_reply && ntlm_reply.has_key?(:target_name)
90:	              vprint_status("#{rhost}:#{rport} Invalid challenge response, aborting...")
91:	              break
92:	            end
93:	
94:	            # TODO: Extract the server name from :target_info as well
95:	            domain = ntlm_reply[:target_name].value.to_s.gsub(/\x00/, '')

<RHOST>:<RPORT> Invalid target name in challenge response, aborting...

Here is a relevant code snippet related to the "<RHOST>:<RPORT> Invalid target name in challenge response, aborting..." error message:

92:	            end
93:	
94:	            # TODO: Extract the server name from :target_info as well
95:	            domain = ntlm_reply[:target_name].value.to_s.gsub(/\x00/, '')
96:	            if domain.to_s.length == 0
97:	              vprint_status("#{rhost}:#{rport} Invalid target name in challenge response, aborting...")
98:	              break
99:	            end
100:	
101:	            print_good("#{rhost}:#{rport} Domain: #{domain}")
102:	            report_note(host: rhost, port: rport, proto: 'tcp', type: 'smtp.ntlm_auth_info', data: { domain: domain })

<RHOST>:<RPORT> Invalid challenge response message, aborting...

Here is a relevant code snippet related to the "<RHOST>:<RPORT> Invalid challenge response message, aborting..." error message:

101:	            print_good("#{rhost}:#{rport} Domain: #{domain}")
102:	            report_note(host: rhost, port: rport, proto: 'tcp', type: 'smtp.ntlm_auth_info', data: { domain: domain })
103:	            break
104:	
105:	          rescue ::Rex::ArgumentError
106:	            vprint_status("#{rhost}:#{rport} Invalid challenge response message, aborting...")
107:	            break
108:	          end
109:	        end
110:	      end
111:

<RHOST>:<RPORT> No NTLM domain found

Here is a relevant code snippet related to the "<RHOST>:<RPORT> No NTLM domain found" error message:

108:	          end
109:	        end
110:	      end
111:	
112:	      if ! domain
113:	        vprint_error("#{rhost}:#{rport} No NTLM domain found")
114:	      end
115:	
116:	    rescue ::Rex::ConnectionRefused, ::Rex::HostUnreachable, ::Rex::ConnectionTimeout, ::Timeout::Error
117:	      # Ignore common networking and response timeout errors
118:	    ensure

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References

See Also

Check also the following modules related to this module:

Authors

  • Rich Whitcroft <rwhitcroft[at]digitalboundary.net>

Version

This page has been produced using Metasploit Framework version 6.1.24-dev. For more modules, visit the Metasploit Module Library.

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