Avoid usage of legacy algorithms on libssl-3.0+

lib/net/ntlm.rb

@@ -59,6 +59,8 @@
 require 'net/ntlm/message/type3'
 
 require 'net/ntlm/encode_util'
+require 'net/ntlm/md4'
+require 'net/ntlm/rc4'
 
 require 'net/ntlm/client'
 require 'net/ntlm/channel_binding'
@@ -124,9 +126,9 @@ def gen_keys(str)
 
       def apply_des(plain, keys)
         keys.map {|k|
-          dec = OpenSSL::Cipher.new("des-cbc").encrypt
+          dec = OpenSSL::Cipher.new("des-ede-cbc").encrypt
           dec.padding = 0
-          dec.key = k
+          dec.key = k + k
           dec.update(plain) + dec.final
         }
       end
@@ -146,7 +148,7 @@ def ntlm_hash(password, opt = {})
         unless opt[:unicode]
           pwd = EncodeUtil.encode_utf16le(pwd)
         end
-        OpenSSL::Digest::MD4.digest pwd
+        Net::NTLM::Md4.digest pwd
       end
 
       # Generate a NTLMv2 Hash

lib/net/ntlm/client/session.rb

@@ -36,11 +36,8 @@ def authenticate!
         t3 = Message::Type3.create type3_opts
         if negotiate_key_exchange?
           t3.enable(:session_key)
-          rc4 = OpenSSL::Cipher.new("rc4")
-          rc4.encrypt
-          rc4.key = user_session_key
-          sk = rc4.update exported_session_key
-          sk << rc4.final
+          rc4 = Net::NTLM::Rc4.new(user_session_key)
+          sk = rc4.encrypt exported_session_key
           t3.session_key = sk
         end
         t3
@@ -50,7 +47,7 @@ def exported_session_key
         @exported_session_key ||=
           begin
             if negotiate_key_exchange?
-              OpenSSL::Cipher.new("rc4").random_key
+              OpenSSL::Random.random_bytes(16)
             else
               user_session_key
             end
@@ -61,8 +58,7 @@ def sign_message(message)
         seq = sequence
         sig = OpenSSL::HMAC.digest(OpenSSL::Digest::MD5.new, client_sign_key, "#{seq}#{message}")[0..7]
         if negotiate_key_exchange?
-          sig = client_cipher.update sig
-          sig << client_cipher.final
+          sig = client_cipher.encrypt sig
         end
         "#{VERSION_MAGIC}#{sig}#{seq}"
       end
@@ -71,20 +67,17 @@ def verify_signature(signature, message)
         seq = signature[-4..-1]
         sig = OpenSSL::HMAC.digest(OpenSSL::Digest::MD5.new, server_sign_key, "#{seq}#{message}")[0..7]
         if negotiate_key_exchange?
-          sig = server_cipher.update sig
-          sig << server_cipher.final
+          sig = server_cipher.encrypt sig
         end
         "#{VERSION_MAGIC}#{sig}#{seq}" == signature
       end
 
       def seal_message(message)
-        emessage = client_cipher.update(message)
-        emessage + client_cipher.final
+        client_cipher.encrypt(message)
       end
 
       def unseal_message(emessage)
-        message = server_cipher.update(emessage)
-        message + server_cipher.final
+        server_cipher.encrypt(emessage)
       end
 
       private
@@ -123,23 +116,11 @@ def server_seal_key
       end
 
       def client_cipher
-        @client_cipher ||=
-          begin
-            rc4 = OpenSSL::Cipher.new("rc4")
-            rc4.encrypt
-            rc4.key = client_seal_key
-            rc4
-          end
+        @client_cipher ||= Net::NTLM::Rc4.new(client_seal_key)
       end
 
       def server_cipher
-        @server_cipher ||=
-          begin
-            rc4 = OpenSSL::Cipher.new("rc4")
-            rc4.decrypt
-            rc4.key = server_seal_key
-            rc4
-          end
+        @server_cipher ||= Net::NTLM::Rc4.new(server_seal_key)
       end
 
       def client_challenge

lib/net/ntlm/md4.rb

@@ -0,0 +1,80 @@
+require 'openssl'
+
+module Net
+module NTLM
+
+  class Md4
+
+    begin
+      OpenSSL::Digest::MD4.digest("")
+    rescue
+      # libssl-3.0+ doesn't support legacy MD4 -> use our own implementation
+
+      require 'stringio'
+
+      def self.digest(string)
+        # functions
+        mask = (1 << 32) - 1
+        f = proc {|x, y, z| x & y | x.^(mask) & z}
+        g = proc {|x, y, z| x & y | x & z | y & z}
+        h = proc {|x, y, z| x ^ y ^ z}
+        r = proc {|v, s| (v << s).&(mask) | (v.&(mask) >> (32 - s))}
+
+        # initial hash
+        a, b, c, d = 0x67452301, 0xefcdab89, 0x98badcfe, 0x10325476
+
+        bit_len = string.size << 3
+        string += "\x80"
+        while (string.size % 64) != 56
+          string += "\0"
+        end
+        string = string.force_encoding('ascii-8bit') + [bit_len & mask, bit_len >> 32].pack("V2")
+
+        if string.size % 64 != 0
+          fail "failed to pad to correct length"
+        end
+
+        io = StringIO.new(string)
+        block = ""
+
+        while io.read(64, block)
+          x = block.unpack("V16")
+
+          # Process this block.
+          aa, bb, cc, dd = a, b, c, d
+          [0, 4, 8, 12].each {|i|
+            a = r[a + f[b, c, d] + x[i],  3]; i += 1
+            d = r[d + f[a, b, c] + x[i],  7]; i += 1
+            c = r[c + f[d, a, b] + x[i], 11]; i += 1
+            b = r[b + f[c, d, a] + x[i], 19]
+          }
+          [0, 1, 2, 3].each {|i|
+            a = r[a + g[b, c, d] + x[i] + 0x5a827999,  3]; i += 4
+            d = r[d + g[a, b, c] + x[i] + 0x5a827999,  5]; i += 4
+            c = r[c + g[d, a, b] + x[i] + 0x5a827999,  9]; i += 4
+            b = r[b + g[c, d, a] + x[i] + 0x5a827999, 13]
+          }
+          [0, 2, 1, 3].each {|i|
+            a = r[a + h[b, c, d] + x[i] + 0x6ed9eba1,  3]; i += 8
+            d = r[d + h[a, b, c] + x[i] + 0x6ed9eba1,  9]; i -= 4
+            c = r[c + h[d, a, b] + x[i] + 0x6ed9eba1, 11]; i += 8
+            b = r[b + h[c, d, a] + x[i] + 0x6ed9eba1, 15]
+          }
+          a = (a + aa) & mask
+          b = (b + bb) & mask
+          c = (c + cc) & mask
+          d = (d + dd) & mask
+        end
+
+        [a, b, c, d].pack("V4")
+      end
+
+    else
+      # Openssl/libssl provides MD4, so we can use it.
+      def self.digest(string)
+        OpenSSL::Digest::MD4.digest(string)
+      end
+    end
+  end
+end
+end

lib/net/ntlm/rc4.rb

@@ -0,0 +1,59 @@
+require 'openssl'
+
+module Net
+module NTLM
+
+  begin
+    OpenSSL::Cipher.new("rc4")
+  rescue
+    # libssl-3.0+ doesn't support legacy Rc4 -> use our own implementation
+
+    class Rc4
+      def initialize(str)
+        raise ArgumentError, "RC4: Key supplied is blank"  if str.eql?('')
+        initialize_state(str)
+        @q1, @q2 = 0, 0
+      end
+
+      def encrypt(text)
+        text.each_byte.map do |b|
+          @q1 = (@q1 + 1) % 256
+          @q2 = (@q2 + @state[@q1]) % 256
+          @state[@q1], @state[@q2] = @state[@q2], @state[@q1]
+          b ^ @state[(@state[@q1] + @state[@q2]) % 256]
+        end.pack("C*")
+      end
+
+      private
+
+      # The initial state which is then modified by the key-scheduling algorithm
+      INITIAL_STATE = (0..255).to_a
+
+      # Performs the key-scheduling algorithm to initialize the state.
+      def initialize_state(key)
+        i = j = 0
+        @state = INITIAL_STATE.dup
+        key_length = key.length
+        while i < 256
+          j = (j + @state[i] + key.getbyte(i % key_length)) % 256
+          @state[i], @state[j] = @state[j], @state[i]
+          i += 1
+        end
+      end
+    end
+
+  else
+    # Openssl/libssl provides RC4, so we can use it.
+    class Rc4
+      def initialize(str)
+        @ci = OpenSSL::Cipher.new("rc4")
+        @ci.key = str
+      end
+
+      def encrypt(text)
+        @ci.update(text) + @ci.final
+      end
+    end
+  end
+end
+end