ruby_smb 3.3.22 → 3.3.23

checksums.yaml

@@ -1,7 +1,7 @@
 ---
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data/lib/ruby_smb/gss/provider/ntlm.rb

@@ -85,7 +85,7 @@ module RubySMB
 
               @server_challenge = @provider.generate_server_challenge
               msg.challenge = @server_challenge.unpack1('Q<') # 64-bit unsigned, little endian (uint64_t)
-              target_info = Net::NTLM::TargetInfo.new('')
+              target_info = Net::NTLM::TargetInfo.new(nil)
               target_info.av_pairs.merge!({
                 Net::NTLM::TargetInfo::MSV_AV_NB_DOMAIN_NAME => @provider.netbios_domain.encode('UTF-16LE').b,
                 Net::NTLM::TargetInfo::MSV_AV_NB_COMPUTER_NAME => @provider.netbios_hostname.encode('UTF-16LE').b,

data/lib/ruby_smb/peer_info.rb

@@ -3,8 +3,10 @@ module RubySMB
     # Extract and store useful information about the peer/server from the
     # NTLM Type 2 (challenge) TargetInfo fields.
     #
-    # @param target_info_str [String] the Target Info string
+    # @param target_info_str [String, nil] the Target Info string
     def store_target_info(target_info_str)
+      return if target_info_str.nil? || target_info_str.empty?
+
       target_info = Net::NTLM::TargetInfo.new(target_info_str)
       {
         Net::NTLM::TargetInfo::MSV_AV_NB_COMPUTER_NAME  => :@default_name,

data/lib/ruby_smb/version.rb

@@ -1,3 +1,3 @@
 module RubySMB
-  VERSION = '3.3.22'.freeze
+  VERSION = '3.3.23'.freeze
 end

data/spec/lib/ruby_smb/client_spec.rb

@@ -1614,6 +1614,15 @@ RSpec.describe RubySMB::Client do
           expect(smb1_client.session_key).to eq ntlm_client.session_key
         end
 
+        it 'continues authentication when the server advertises empty target info' do
+          challenge = Net::NTLM::Message.decode64(type2_string)
+          challenge.set_flag(:TARGET_INFO)
+          challenge.target_info = ''.b
+          allow(smb1_client).to receive(:smb1_type2_message).and_return(challenge.encode64)
+
+          expect(smb1_client.smb1_authenticate).to eq WindowsError::NTStatus::STATUS_SUCCESS
+        end
+
         it 'stores the OS version number from the challenge message' do
           smb1_client.smb1_authenticate
           expect(smb1_client.os_version).to eq '6.1.7601'
@@ -1860,6 +1869,15 @@ RSpec.describe RubySMB::Client do
           expect(smb2_client.session_key).to eq ntlm_client.session_key
         end
 
+        it 'continues authentication when the server advertises empty target info' do
+          challenge = Net::NTLM::Message.decode64(type2_string)
+          challenge.set_flag(:TARGET_INFO)
+          challenge.target_info = ''.b
+          allow(smb2_client).to receive(:smb2_type2_message).and_return(challenge.encode64)
+
+          expect(smb2_client.smb2_authenticate).to eq WindowsError::NTStatus::STATUS_SUCCESS
+        end
+
         it 'stores the OS version number from the challenge message' do
           smb2_client.smb2_authenticate
           expect(smb2_client.os_version).to eq '6.1.7601'
@@ -2068,6 +2086,25 @@ RSpec.describe RubySMB::Client do
         client.store_target_info(target_info_str)
       end
 
+      it 'preserves existing peer information when given empty target info' do
+        client.store_target_info(target_info_str)
+        expect { client.store_target_info(''.b) }.to_not change {
+          [client.default_name, client.default_domain, client.dns_host_name, client.dns_domain_name, client.dns_tree_name]
+        }
+      end
+
+      it 'accepts nil target info' do
+        expect { client.store_target_info(nil) }.to_not raise_error
+      end
+
+      it 'accepts empty target info encoded with an end-of-list marker' do
+        expect { client.store_target_info("\x00\x00\x00\x00".b) }.to_not raise_error
+      end
+
+      it 'rejects nonempty invalid target info' do
+        expect { client.store_target_info("\xff\xff\x00\x00".b) }.to raise_error(Net::NTLM::InvalidTargetDataError)
+      end
+
       it 'sets the expected Client\'s attribute' do
         client.store_target_info(target_info_str)
         expect(client.default_name).to eq 'TESTNAME'

data/spec/lib/ruby_smb/dcerpc/client_spec.rb

@@ -173,6 +173,14 @@ RSpec.describe RubySMB::Dcerpc::Client do
         expect(auth_client.process_ntlm_type2(type2_message)).to start_with("NTLMSSP\x00\x03\x00\x00\x00")
       end
 
+      it 'returns a type3 message when the server advertises empty target info' do
+        challenge = Net::NTLM::Message.parse(type2_message)
+        challenge.set_flag(:TARGET_INFO)
+        challenge.target_info = ''.b
+
+        expect(auth_client.process_ntlm_type2(challenge.serialize)).to start_with("NTLMSSP\x00\x03\x00\x00\x00")
+      end
+
       it 'stores the session key' do
         auth_client.process_ntlm_type2(type2_message)
         expect(auth_client.instance_variable_get(:@session_key).size).to eq(16)

data/spec/lib/ruby_smb/gss/provider/ntlm/authenticator_spec.rb

@@ -65,6 +65,19 @@ RSpec.describe RubySMB::Gss::Provider::NTLM::Authenticator do
     it 'should process a NTLM type 1 message and return a type2 message' do
       expect(authenticator.process_ntlm_type1(type1_msg)).to be_a Net::NTLM::Message::Type2
     end
+
+    it 'includes the server names in the serialized target info' do
+      type2_msg = Net::NTLM::Message.parse(authenticator.process_ntlm_type1(type1_msg).serialize)
+      target_info = Net::NTLM::TargetInfo.new(type2_msg.target_info)
+
+      expect(target_info.av_pairs).to include(
+        Net::NTLM::TargetInfo::MSV_AV_NB_DOMAIN_NAME => provider.netbios_domain.encode('UTF-16LE').b,
+        Net::NTLM::TargetInfo::MSV_AV_NB_COMPUTER_NAME => provider.netbios_hostname.encode('UTF-16LE').b,
+        Net::NTLM::TargetInfo::MSV_AV_DNS_DOMAIN_NAME => provider.dns_domain.encode('UTF-16LE').b,
+        Net::NTLM::TargetInfo::MSV_AV_DNS_COMPUTER_NAME => provider.dns_hostname.encode('UTF-16LE').b
+      )
+      expect(target_info.av_pairs[Net::NTLM::TargetInfo::MSV_AV_TIMESTAMP].bytesize).to eq 8
+    end
   end
 
   describe '#process_ntlm_type3' do

data/spec/lib/ruby_smb/ntlm/client/session_spec.rb

@@ -8,7 +8,9 @@ RSpec.describe RubySMB::NTLM::Client::Session do
     AGwAbwBjAGEAbAADADgAVwBJAE4ALQAzAE0AUwBQADgASwAyAEwAQwBHAEMA
     LgBtAHMAZgBsAGEAYgAuAGwAbwBjAGEAbAAHAAgAS6UAWjxl2AEAAAAA
   }) }
-  subject(:client) { RubySMB::NTLM::Client.new('rubysmb', 'rubysmb', flags: RubySMB::NTLM::DEFAULT_CLIENT_FLAGS) }
+  let(:username) { 'rubysmb' }
+  let(:password) { 'rubysmb' }
+  let(:client) { RubySMB::NTLM::Client.new(username, password, flags: RubySMB::NTLM::DEFAULT_CLIENT_FLAGS) }
   subject(:session) { described_class.new(client, message) }
 
   describe '#authenticate!' do
@@ -17,72 +19,49 @@ RSpec.describe RubySMB::NTLM::Client::Session do
       session.authenticate!
     end
 
-    it 'checks if it is anonymous' do
-      expect(session).to receive(:is_anonymous?).at_least(1).times.and_call_original
-      session.authenticate!
-    end
-
     it 'returns a Type3 message' do
       expect(session.authenticate!).to be_a Net::NTLM::Message::Type3
       expect(session.authenticate!).to be_a Net::NTLM::Message
     end
 
     context 'when it is anonymous' do
-      before(:each) { allow(session).to receive(:is_anonymous?).and_return(true) }
-      after(:each) { session.authenticate! }
+      let(:username) { '' }
+      let(:password) { '' }
 
       it 'uses the correct lm response' do
-        expect(session).to_not receive(:lmv2_resp)
-        expect(Net::NTLM::Message::Type3).to receive(:create).and_wrap_original do |method, params|
-          expect(params).to include :lm_response
-          expect(params[:lm_response]).to eq "\x00".b
-          method.call(params)
-        end
+        expect(session.authenticate!.lm_response).to eq "\x00".b
       end
 
       it 'uses the correct ntlm response' do
-        expect(session).to_not receive(:ntlmv2_resp)
-        expect(Net::NTLM::Message::Type3).to receive(:create).and_wrap_original do |method, params|
-          expect(params).to include :ntlm_response
-          expect(params[:ntlm_response]).to eq ''
-          method.call(params)
-        end
+        expect(session.authenticate!.ntlm_response).to eq ''
       end
     end
 
     context 'when it is not anonymous' do
-      before(:each) { allow(session).to receive(:is_anonymous?).and_return(false) }
-      after(:each) { session.authenticate! }
-
       it 'uses the correct lm response' do
-        expect(session).to receive(:lmv2_resp).and_call_original
-        expect(Net::NTLM::Message::Type3).to receive(:create).and_wrap_original do |method, params|
-          expect(params).to include :lm_response
-          expect(params[:lm_response].length).to be > 16
-          method.call(params)
-        end
+        expect(session.authenticate!.lm_response.length).to be > 16
       end
 
       it 'uses the correct ntlm response' do
-        expect(session).to receive(:ntlmv2_resp).and_call_original
-        expect(Net::NTLM::Message::Type3).to receive(:create).and_wrap_original do |method, params|
-          expect(params).to include :ntlm_response
-          expect(params[:ntlm_response].length).to be > 16
-          method.call(params)
-        end
+        expect(session.authenticate!.ntlm_response.length).to be > 16
       end
     end
   end
 
   describe '#calculate_user_session_key!' do
-    it 'returns an all zero key when it is anonymous' do
-      expect(session).to receive(:is_anonymous?).and_return(true)
-      expect(session.send(:calculate_user_session_key!)).to eq "\x00".b * 16
+    context 'when it is anonymous' do
+      let(:username) { '' }
+      let(:password) { '' }
+
+      it 'returns an all zero key' do
+        expect(session.send(:calculate_user_session_key!)).to eq "\x00".b * 16
+      end
     end
 
     it 'returns a session key' do
-      expect(session).to receive(:is_anonymous?).and_return(false)
-      expect(session.send(:calculate_user_session_key!)).to_not eq "\x00".b * 16
+      session_key = session.send(:calculate_user_session_key!)
+      expect(session_key.bytesize).to eq 16
+      expect(session_key).to_not eq "\x00".b * 16
     end
   end
 

metadata

@@ -1,7 +1,7 @@
 --- !ruby/object:Gem::Specification
 name: ruby_smb
 version: !ruby/object:Gem::Version
-  version: 3.3.22
+  version: 3.3.23
 platform: ruby
 authors:
 - Metasploit Hackers
@@ -13,7 +13,7 @@ authors:
 autorequire:
 bindir: bin
 cert_chain: []
-date: 2026-07-31 00:00:00.000000000 Z
+date: 2026-09-28 00:00:00.000000000 Z
 dependencies:
 - !ruby/object:Gem::Dependency
   name: redcarpet