[release/8.0] Fix NegotiateStream connections between Linux clients and Windows servers (#102216)

* Fix NegotiateStream connections between Linux clients and Windows servers (#99909)

* Send the NegotiateSeal NTLM flag when client asked for
ProtectionLevel.EncryptAndSign.

Process the last handshake done message in NegotiateStream. In case of
SPNEGO protocol it may contain message integrity check. Additionally,
if the negotiated protocol is NTLM then we need to reset the encryption
key after the message integrity check is verified.

* Add test for the NegotiateSeal flag

* Fix the test

* Dummy commit

* Fix the new _remoteOk logic in NegotiateStream to fire only when HandshakeComplete.

If HandshakeComplete is not true, then the authentication blob will get processed with the normal flow.

* Fix the value of NegotiateSeal in the final authentication message of Managed NTLM

* Fix build

* Remove unwanted test change

---------

Co-authored-by: Filip Navara <[email protected]>
Co-authored-by: wfurt <[email protected]>

Author: 3 people

src/libraries/Common/tests/System/Net/Security/FakeNtlmServer.cs

@@ -42,6 +42,8 @@ public FakeNtlmServer(NetworkCredential expectedCredential)
         public bool IsAuthenticated { get; private set; }
         public bool IsMICPresent { get; private set; }
         public string? ClientSpecifiedSpn { get; private set; }
+        public Flags InitialClientFlags { get; private set; }
+        public Flags NegotiatedFlags => _negotiatedFlags;
 
         private NetworkCredential _expectedCredential;
 
@@ -83,7 +85,7 @@ private enum MessageType : uint
         }
 
         [Flags]
-        private enum Flags : uint
+        public enum Flags : uint
         {
             NegotiateUnicode = 0x00000001,
             NegotiateOEM = 0x00000002,
@@ -177,17 +179,17 @@ private static ReadOnlySpan<byte> GetField(ReadOnlySpan<byte> payload, int field
                 case MessageType.Negotiate:
                     // We don't negotiate, we just verify
                     Assert.True(incomingBlob.Length >= 32);
-                    Flags flags = (Flags)BinaryPrimitives.ReadUInt32LittleEndian(incomingBlob.AsSpan(12, 4));
-                    Assert.Equal(_requiredFlags, (flags & _requiredFlags));
-                    Assert.True((flags & (Flags.NegotiateOEM | Flags.NegotiateUnicode)) != 0);
-                    if (flags.HasFlag(Flags.NegotiateDomainSupplied))
+                    InitialClientFlags = (Flags)BinaryPrimitives.ReadUInt32LittleEndian(incomingBlob.AsSpan(12, 4));
+                    Assert.Equal(_requiredFlags, (InitialClientFlags & _requiredFlags));
+                    Assert.True((InitialClientFlags & (Flags.NegotiateOEM | Flags.NegotiateUnicode)) != 0);
+                    if (InitialClientFlags.HasFlag(Flags.NegotiateDomainSupplied))
                     {
                         string domain = Encoding.ASCII.GetString(GetField(incomingBlob, 16));
                         Assert.Equal(_expectedCredential.Domain, domain);
                     }
                     _expectedMessageType = MessageType.Authenticate;
                     _negotiateMessage = incomingBlob;
-                    return _challengeMessage = GenerateChallenge(flags);
+                    return _challengeMessage = GenerateChallenge(InitialClientFlags);
 
                 case MessageType.Authenticate:
                     // Validate the authentication!

src/libraries/System.Net.Security/src/System/Net/NegotiateAuthenticationPal.ManagedNtlm.cs

@@ -262,8 +262,14 @@ public override void Dispose()
                 {
                     Debug.Assert(incomingBlob.IsEmpty);
 
+                    Flags requiredFlags = s_requiredFlags;
+                    if (_protectionLevel == ProtectionLevel.EncryptAndSign)
+                    {
+                        requiredFlags |= Flags.NegotiateSeal;
+                    }
+
                     _negotiateMessage = new byte[sizeof(NegotiateMessage)];
-                    CreateNtlmNegotiateMessage(_negotiateMessage);
+                    CreateNtlmNegotiateMessage(_negotiateMessage, requiredFlags);
 
                     outgoingBlob = _negotiateMessage;
                     statusCode = NegotiateAuthenticationStatusCode.ContinueNeeded;
@@ -278,7 +284,7 @@ public override void Dispose()
                 return outgoingBlob;
             }
 
-            private static unsafe void CreateNtlmNegotiateMessage(Span<byte> asBytes)
+            private static unsafe void CreateNtlmNegotiateMessage(Span<byte> asBytes, Flags requiredFlags)
             {
                 Debug.Assert(HeaderLength == NtlmHeader.Length);
                 Debug.Assert(asBytes.Length == sizeof(NegotiateMessage));
@@ -288,7 +294,7 @@ private static unsafe void CreateNtlmNegotiateMessage(Span<byte> asBytes)
                 asBytes.Clear();
                 NtlmHeader.CopyTo(asBytes);
                 message.Header.MessageType = MessageType.Negotiate;
-                message.Flags = s_requiredFlags;
+                message.Flags = requiredFlags;
                 message.Version = s_version;
             }
 
@@ -573,6 +579,13 @@ private static byte[] DeriveKey(ReadOnlySpan<byte> exportedSessionKey, ReadOnlyS
                     return null;
                 }
 
+                // We already negotiate signing, so we only need to check sealing/encryption.
+                if ((flags & Flags.NegotiateSeal) == 0 && _protectionLevel == ProtectionLevel.EncryptAndSign)
+                {
+                    statusCode = NegotiateAuthenticationStatusCode.QopNotSupported;
+                    return null;
+                }
+
                 ReadOnlySpan<byte> targetInfo = GetField(challengeMessage.TargetInfo, blob);
                 byte[] targetInfoBuffer = ProcessTargetInfo(targetInfo, out DateTime time, out bool hasNbNames);
 
@@ -607,7 +620,7 @@ private static byte[] DeriveKey(ReadOnlySpan<byte> exportedSessionKey, ReadOnlyS
                 NtlmHeader.CopyTo(responseAsSpan);
 
                 response.Header.MessageType = MessageType.Authenticate;
-                response.Flags = s_requiredFlags;
+                response.Flags = s_requiredFlags | (flags & Flags.NegotiateSeal);
                 response.Version = s_version;
 
                 // Calculate hash for hmac - same for lm2 and ntlm2

src/libraries/System.Net.Security/src/System/Net/Security/NegotiateStream.cs

@@ -883,7 +883,16 @@ private async Task ReceiveBlobAsync<TIOAdapter>(CancellationToken cancellationTo
 
             if (_framer.ReadHeader.MessageId == FrameHeader.HandshakeDoneId)
             {
-                _remoteOk = true;
+                if (HandshakeComplete && message.Length > 0)
+                {
+                    Debug.Assert(_context != null);
+                    _context.GetOutgoingBlob(message, out NegotiateAuthenticationStatusCode statusCode);
+                    _remoteOk = statusCode is NegotiateAuthenticationStatusCode.Completed;
+                }
+                else
+                {
+                    _remoteOk = true;
+                }
             }
             else if (_framer.ReadHeader.MessageId != FrameHeader.HandshakeId)
             {

src/libraries/System.Net.Security/tests/UnitTests/NegotiateAuthenticationTests.cs

@@ -190,6 +190,42 @@ public void NtlmIncorrectExchangeTest()
             Assert.False(fakeNtlmServer.IsAuthenticated);
         }
 
+        [ConditionalFact(nameof(IsNtlmAvailable))]
+        public void NtlmEncryptionTest()
+        {
+            using FakeNtlmServer fakeNtlmServer = new FakeNtlmServer(s_testCredentialRight);
+
+            NegotiateAuthentication ntAuth = new NegotiateAuthentication(
+                new NegotiateAuthenticationClientOptions
+                {
+                    Package = "NTLM",
+                    Credential = s_testCredentialRight,
+                    TargetName = "HTTP/foo",
+                    RequiredProtectionLevel = ProtectionLevel.EncryptAndSign
+                });
+
+            NegotiateAuthenticationStatusCode statusCode;
+            byte[]? negotiateBlob = ntAuth.GetOutgoingBlob((byte[])null, out statusCode);
+            Assert.Equal(NegotiateAuthenticationStatusCode.ContinueNeeded, statusCode);
+            Assert.NotNull(negotiateBlob);
+
+            byte[]? challengeBlob = fakeNtlmServer.GetOutgoingBlob(negotiateBlob);
+            Assert.NotNull(challengeBlob);
+            // Validate that the client sent NegotiateSeal flag
+            Assert.Equal(FakeNtlmServer.Flags.NegotiateSeal, (fakeNtlmServer.InitialClientFlags & FakeNtlmServer.Flags.NegotiateSeal));
+
+            byte[]? authenticateBlob = ntAuth.GetOutgoingBlob(challengeBlob, out statusCode);
+            Assert.Equal(NegotiateAuthenticationStatusCode.Completed, statusCode);
+            Assert.NotNull(authenticateBlob);
+
+            byte[]? empty = fakeNtlmServer.GetOutgoingBlob(authenticateBlob);
+            Assert.Null(empty);
+            Assert.True(fakeNtlmServer.IsAuthenticated);
+
+            // Validate that the NegotiateSeal flag survived the full exchange
+            Assert.Equal(FakeNtlmServer.Flags.NegotiateSeal, (fakeNtlmServer.NegotiatedFlags & FakeNtlmServer.Flags.NegotiateSeal));
+        }
+
         [ConditionalFact(nameof(IsNtlmAvailable))]
         [ActiveIssue("https://github.com/dotnet/runtime/issues/65678", TestPlatforms.OSX | TestPlatforms.iOS | TestPlatforms.MacCatalyst)]
         public void NtlmSignatureTest()
@@ -218,7 +254,7 @@ public void NtlmSignatureTest()
             fakeNtlmServer.Unwrap(output.WrittenSpan, temp);
             Assert.Equal(s_Hello, temp);
 
-            // Test creating signature on server side and decoding it with VerifySignature on client side 
+            // Test creating signature on server side and decoding it with VerifySignature on client side
             byte[] serverSignedMessage = new byte[16 + s_Hello.Length];
             fakeNtlmServer.Wrap(s_Hello, serverSignedMessage);
             output.Clear();