# -*- coding: binary -*- # # An NTLM Authentication Library for Ruby # # This code is a derivative of "dbf2.rb" written by yrock # and Minero Aoki. You can find original code here: # http://jp.rubyist.net/magazine/?0013-CodeReview # ------------------------------------------------------------- # Copyright (c) 2005,2006 yrock # # This program is free software. # You can distribute/modify this program under the terms of the # Ruby License. # # 2011-03-08 improved through a code merge with Metasploit's SMB::Crypt # ------------------------------------------------------------- # # 2011-02-23 refactored and improved by Alexandre Maloteaux for Metasploit Project # ------------------------------------------------------------- # # 2006-02-11 refactored by Minero Aoki # ------------------------------------------------------------- # # All protocol information used to write this code stems from # "The NTLM Authentication Protocol" by Eric Glass. The author # would thank to him for this tremendous work and making it # available on the net. # http://davenport.sourceforge.net/ntlm.html # ------------------------------------------------------------- # Copyright (c) 2003 Eric Glass # # Permission to use, copy, modify, and distribute this document # for any purpose and without any fee is hereby granted, # provided that the above copyright notice and this list of # conditions appear in all copies. # ------------------------------------------------------------- # # The author also looked Mozilla-Firefox-1.0.7 source code, # namely, security/manager/ssl/src/nsNTLMAuthModule.cpp and # Jonathan Bastien-Filiatrault's libntlm-ruby. # "http://x2a.org/websvn/filedetails.php? # repname=libntlm-ruby&path=%2Ftrunk%2Fntlm.rb&sc=1" # The latter has a minor bug in its separate_keys function. # The third key has to begin from the 14th character of the # input string instead of 13th:) #-- # $Id: ntlm.rb 11678 2011-01-30 19:26:35Z hdm $ #++ require 'rex/proto/ntlm/constants' require 'rex/proto/ntlm/base' module Rex module Proto module NTLM class Crypt CONST = Rex::Proto::NTLM::Constants BASE = Rex::Proto::NTLM::Base @@loaded_openssl = false begin require 'openssl' require 'openssl/digest' @@loaded_openssl = true rescue ::Exception end def self.gen_keys(str) str.scan(/.{7}/).map{ |key| des_56_to_64(key) } end def self.des_56_to_64(ckey56s) ckey64 = [] ckey56 = ckey56s.unpack('C*') ckey64[0] = ckey56[0] ckey64[1] = ((ckey56[0] << 7) & 0xFF) | (ckey56[1] >> 1) ckey64[2] = ((ckey56[1] << 6) & 0xFF) | (ckey56[2] >> 2) ckey64[3] = ((ckey56[2] << 5) & 0xFF) | (ckey56[3] >> 3) ckey64[4] = ((ckey56[3] << 4) & 0xFF) | (ckey56[4] >> 4) ckey64[5] = ((ckey56[4] << 3) & 0xFF) | (ckey56[5] >> 5) ckey64[6] = ((ckey56[5] << 2) & 0xFF) | (ckey56[6] >> 6) ckey64[7] = (ckey56[6] << 1) & 0xFF ckey64.pack('C*') end def self.apply_des(plain, keys) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl dec = OpenSSL::Cipher::DES.new keys.map do |k| dec.key = k dec.encrypt.update(plain) end end def self.lm_hash(password, half = false) size = half ? 7 : 14 keys = gen_keys(password.upcase.ljust(size, "\0")) apply_des(CONST::LM_MAGIC, keys).join end def self.ntlm_hash(password, opt = {}) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl pwd = password.dup unless opt[:unicode] pwd = Rex::Text.to_unicode(pwd) end OpenSSL::Digest::MD4.digest(pwd) end # This hash is used for lmv2/ntlmv2 response calculation def self.ntlmv2_hash(user, password, domain, opt={}) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl if opt[:pass_is_hash] ntlmhash = password else ntlmhash = ntlm_hash(password, opt) end # With Win 7 and maybe other OSs we sometimes get the domain not uppercased userdomain = user.upcase + domain unless opt[:unicode] userdomain = Rex::Text.to_unicode(userdomain) end OpenSSL::HMAC.digest(OpenSSL::Digest::MD5.new, ntlmhash, userdomain) end # Create the LANMAN response def self.lm_response(arg, half = false) begin hash = arg[:lm_hash] chal = arg[:challenge] rescue raise ArgumentError end chal = BASE::pack_int64le(chal) if chal.is_a?(Integer) if half then size = 7 else size = 21 end keys = gen_keys hash.ljust(size, "\0") apply_des(chal, keys).join end # Synonym of lm_response for old compatibility with lib/rex/proto/smb/crypt def self.lanman_des(password, challenge) lm_response({ :lm_hash => self.lm_hash(password), :challenge => challenge }) end def self.ntlm_response(arg) hash = arg[:ntlm_hash] chal = arg[:challenge] chal = BASE::pack_int64le(chal) if chal.is_a?(::Integer) keys = gen_keys(hash.ljust(21, "\0")) apply_des(chal, keys).join end #synonym of ntlm_response for old compatibility with lib/rex/proto/smb/crypt def self.ntlm_md4(password, challenge) ntlm_response({ :ntlm_hash => self.ntlm_hash(password), :challenge => challenge }) end def self.ntlmv2_response(arg, opt = {}) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl key, chal = arg[:ntlmv2_hash], arg[:challenge] if not (key and chal) raise ArgumentError , 'ntlmv2_hash and challenge are mandatory' end chal = BASE::pack_int64le(chal) if chal.is_a?(::Integer) bb = nil if opt[:nt_client_challenge] if opt[:nt_client_challenge].to_s.length <= 8 raise ArgumentError,"nt_client_challenge is not in a correct format " end bb = opt[:nt_client_challenge] else if not arg[:target_info] raise ArgumentError, "target_info is mandatory in this case" end ti = arg[:target_info] cc = opt[:client_challenge] || rand(CONST::MAX64) cc = BASE::pack_int64le(cc) if cc.is_a?(::Integer) ts = opt[:timestamp] || Time.now.to_i # Convert the unix timestamp to windows format # epoch -> milsec from Jan 1, 1601 ts = 10000000 * (ts + CONST::TIME_OFFSET) blob = BASE::Blob.new blob.timestamp = ts blob.challenge = cc blob.target_info = ti bb = blob.serialize end OpenSSL::HMAC.digest(OpenSSL::Digest::MD5.new, key, chal + bb) + bb end def self.lmv2_response(arg, opt = {}) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl key = arg[:ntlmv2_hash] chal = arg[:challenge] chal = BASE::pack_int64le(chal) if chal.is_a?(::Integer) cc = opt[:client_challenge] || rand(CONST::MAX64) cc = BASE::pack_int64le(cc) if cc.is_a?(::Integer) OpenSSL::HMAC.digest(OpenSSL::Digest::MD5.new, key, chal + cc) + cc end def self.ntlm2_session(arg, opt = {}) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl passwd_hash,chal = arg[:ntlm_hash],arg[:challenge] if not (passwd_hash and chal) raise RuntimeError, "ntlm_hash and challenge are required" end cc = opt[:client_challenge] || rand(CONST::MAX64) cc = BASE::pack_int64le(cc) if cc.is_a?(Integer) keys = gen_keys(passwd_hash.ljust(21, "\0")) session_hash = OpenSSL::Digest::MD5.digest(chal + cc)[0,8] response = apply_des(session_hash, keys).join [cc.ljust(24, "\0"), response] end #this function will check if the net lm response provided correspond to en empty password def self.is_hash_from_empty_pwd?(arg) hash_type = arg[:type] raise ArgumentError,"arg[:type] is mandatory" if not hash_type raise ArgumentError,"arg[:type] must be lm or ntlm" if not hash_type =~ /^((lm)|(ntlm))$/ ntlm_ver = arg[:ntlm_ver] raise ArgumentError,"arg[:ntlm_ver] is mandatory" if not ntlm_ver hash = arg[:hash] raise ArgumentError,"arg[:hash] is mandatory" if not hash srv_chall = arg[:srv_challenge] raise ArgumentError,"arg[:srv_challenge] is mandatory" if not srv_chall raise ArgumentError,"Server challenge length must be exactly 8 bytes" if srv_chall.length != 8 #calculate responses for empty pwd case ntlm_ver when CONST::NTLM_V1_RESPONSE if hash.length != 24 raise ArgumentError,"hash length must be exactly 24 bytes " end case hash_type when 'lm' arglm = { :lm_hash => self.lm_hash(''), :challenge => srv_chall} calculatedhash = self.lm_response(arglm) when 'ntlm' argntlm = { :ntlm_hash => self.ntlm_hash(''), :challenge => srv_chall } calculatedhash = self.ntlm_response(argntlm) end when CONST::NTLM_V2_RESPONSE raise ArgumentError,"hash length must be exactly 16 bytes " if hash.length != 16 cli_chall = arg[:cli_challenge] raise ArgumentError,"arg[:cli_challenge] is mandatory in this case" if not cli_chall user = arg[:user] raise ArgumentError,"arg[:user] is mandatory in this case" if not user domain = arg[:domain] raise ArgumentError,"arg[:domain] is mandatory in this case" if not domain case hash_type when 'lm' raise ArgumentError,"Client challenge length must be exactly 8 bytes " if cli_chall.length != 8 arglm = { :ntlmv2_hash => self.ntlmv2_hash(user,'', domain), :challenge => srv_chall } optlm = { :client_challenge => cli_chall} calculatedhash = self.lmv2_response(arglm, optlm)[0,16] when 'ntlm' raise ArgumentError,"Client challenge length must be bigger then 8 bytes " if cli_chall.length <= 8 argntlm = { :ntlmv2_hash => self.ntlmv2_hash(user, '', domain), :challenge => srv_chall } optntlm = { :nt_client_challenge => cli_chall} calculatedhash = self.ntlmv2_response(argntlm,optntlm)[0,16] end when CONST::NTLM_2_SESSION_RESPONSE raise ArgumentError,"hash length must be exactly 16 bytes " if hash.length != 24 cli_chall = arg[:cli_challenge] raise ArgumentError,"arg[:cli_challenge] is mandatory in this case" if not cli_chall raise ArgumentError,"Client challenge length must be exactly 8 bytes " if cli_chall.length != 8 case hash_type when 'lm' raise ArgumentError, "ntlm2_session is incompatible with lm" when 'ntlm' argntlm = { :ntlm_hash => self.ntlm_hash(''), :challenge => srv_chall } optntlm = { :client_challenge => cli_chall} end calculatedhash = self.ntlm2_session(argntlm,optntlm).join[24,24] else raise ArgumentError,"ntlm_ver is of unknow type" end hash == calculatedhash end # # Signing method added for metasploit project # # Used when only the LMv1 response is provided (i.e., with Win9x clients) def self.lmv1_user_session_key(pass, opt = {}) if opt[:pass_is_hash] usk = pass[0,8] else usk = self.lm_hash(pass.upcase[0,7],true) end usk.ljust(16,"\x00") end # This variant is used when the client sends the NTLMv1 response def self.ntlmv1_user_session_key(pass, opt = {}) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl if opt[:pass_is_hash] usk = pass else usk = self.ntlm_hash(pass) end OpenSSL::Digest::MD4.digest(usk) end # Used when NTLMv1 authentication is employed with NTLM2 session security def self.ntlm2_session_user_session_key(pass, srv_chall, cli_chall, opt = {}) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl ntlm_key = self.ntlmv1_user_session_key(pass, opt ) session_chal = srv_chall + cli_chall OpenSSL::HMAC.digest(OpenSSL::Digest::MD5.new, ntlm_key, session_chal) end # Used when the LMv2 response is sent def self.lmv2_user_session_key(user, pass, domain, srv_chall, cli_chall, opt = {}) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl ntlmv2_key = self.ntlmv2_hash(user, pass, domain, opt) hash1 = OpenSSL::HMAC.digest(OpenSSL::Digest::MD5.new, ntlmv2_key, srv_chall + cli_chall) OpenSSL::HMAC.digest(OpenSSL::Digest::MD5.new, ntlmv2_key, hash1) end # Used when the NTLMv2 response is sent class << self; alias_method :ntlmv2_user_session_key, :lmv2_user_session_key; end # Used when LanMan Key flag is set def self.lanman_session_key(pass, srvchall, opt = {}) if opt[:pass_is_hash] halfhash = pass[0,8] else halfhash = lm_hash(pass.upcase[0,7],true) end plain = self.lm_response({ :lm_hash => halfhash[0,7], :challenge => srvchall }, true ) key = halfhash + ["bdbdbdbdbdbd"].pack("H*") keys = self.gen_keys(key) apply_des(plain, keys).join end def self.encrypt_sessionkey(session_key, user_session_key) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl cipher = OpenSSL::Cipher::Cipher.new('rc4') cipher.encrypt cipher.key = user_session_key cipher.update(session_key) end def self.decrypt_sessionkey(encrypted_session_key, user_session_key) raise RuntimeError, "No OpenSSL support" if not @@loaded_openssl cipher = OpenSSL::Cipher::Cipher.new('rc4') cipher.decrypt cipher.key = user_session_key cipher.update(encrypted_session_key) end def self.make_weak_sessionkey(session_key,key_size,lanman_key = false) case key_size when 40 if lanman_key return session_key[0,5] + "\xe5\x38\xb0" else return session_key[0,5] end when 56 if lanman_key return session_key[0,7] + "\xa0" else return session_key[0,7] end else #128 return session_key[0,16] end end end end end end