diff --git a/src/libraries/Common/tests/System/Net/Security/FakeNtlmServer.cs b/src/libraries/Common/tests/System/Net/Security/FakeNtlmServer.cs
index 6f576d927b2190..af19e91106cb19 100644
--- a/src/libraries/Common/tests/System/Net/Security/FakeNtlmServer.cs
+++ b/src/libraries/Common/tests/System/Net/Security/FakeNtlmServer.cs
@@ -37,6 +37,8 @@ public FakeNtlmServer(NetworkCredential expectedCredential)
         public bool TargetIsServer { get; set; } = false;
         public bool PreferUnicode { get; set; } = true;
         public bool ForceNegotiateVersion { get; set; } = true;
+        public bool SendPreExistingTargetName { get; set; } = false;
+        public bool SendPreExistingChannelBindings { get; set; } = false;
 
         // Negotiation results
         public bool IsAuthenticated { get; private set; }
@@ -261,6 +263,21 @@ private byte[] GenerateChallenge(Flags flags)
                 targetInfoCurrentOffset += 12;
             }
 
+            if (SendPreExistingTargetName)
+            {
+                // Insert a dummy TargetName AV pair that the client should replace with its own
+                targetInfoCurrentOffset += WriteAvIdString(buffer.AsSpan(targetInfoCurrentOffset), AvId.TargetName, "DummyTargetName");
+            }
+
+            if (SendPreExistingChannelBindings)
+            {
+                // Insert a dummy ChannelBindings AV pair (16 zero bytes) that the client should replace
+                BinaryPrimitives.WriteUInt16LittleEndian(buffer.AsSpan(targetInfoCurrentOffset), (ushort)AvId.ChannelBindings);
+                BinaryPrimitives.WriteUInt16LittleEndian(buffer.AsSpan(targetInfoCurrentOffset + 2), (ushort)16);
+                // Leave channel bindings hash as zeros (dummy value)
+                targetInfoCurrentOffset += 20;
+            }
+
             // TODO: DNS machine, domain, forest?
             // EOL
             targetInfoCurrentOffset += 4;
diff --git a/src/libraries/System.Net.Security/src/System/Net/NegotiateAuthenticationPal.ManagedNtlm.cs b/src/libraries/System.Net.Security/src/System/Net/NegotiateAuthenticationPal.ManagedNtlm.cs
index d8909a897dbef6..497d95f06e24c6 100644
--- a/src/libraries/System.Net.Security/src/System/Net/NegotiateAuthenticationPal.ManagedNtlm.cs
+++ b/src/libraries/System.Net.Security/src/System/Net/NegotiateAuthenticationPal.ManagedNtlm.cs
@@ -560,7 +560,7 @@ private byte[] ProcessTargetInfo(ReadOnlySpan<byte> targetInfo, out DateTime tim
                     return targetInfoBuffer;
                 }
 
-                return targetInfoBuffer.AsSpan(targetInfoOffset).ToArray();
+                return targetInfoBuffer.AsSpan(0, targetInfoOffset).ToArray();
             }
 
             // Section 3.4.5.2 SIGNKEY, 3.4.5.3 SEALKEY
diff --git a/src/libraries/System.Net.Security/tests/UnitTests/NegotiateAuthenticationTests.cs b/src/libraries/System.Net.Security/tests/UnitTests/NegotiateAuthenticationTests.cs
index 016f4f63192ab6..7ccc7dd1a8d7eb 100644
--- a/src/libraries/System.Net.Security/tests/UnitTests/NegotiateAuthenticationTests.cs
+++ b/src/libraries/System.Net.Security/tests/UnitTests/NegotiateAuthenticationTests.cs
@@ -347,6 +347,31 @@ private void DoNtlmExchange(FakeNtlmServer fakeNtlmServer, NegotiateAuthenticati
             Assert.Null(empty);
         }
 
+        [ConditionalTheory(typeof(NegotiateAuthenticationTests), nameof(UseManagedNtlm))]
+        [InlineData(true, false)]
+        [InlineData(false, true)]
+        [InlineData(true, true)]
+        public void NtlmWithPreExistingTargetInfoEntriesTest(bool sendPreExistingTargetName, bool sendPreExistingChannelBindings)
+        {
+            using FakeNtlmServer fakeNtlmServer = new FakeNtlmServer(s_testCredentialRight)
+            {
+                SendPreExistingTargetName = sendPreExistingTargetName,
+                SendPreExistingChannelBindings = sendPreExistingChannelBindings,
+            };
+            NegotiateAuthentication ntAuth = new NegotiateAuthentication(
+                new NegotiateAuthenticationClientOptions
+                {
+                    Package = "NTLM",
+                    Credential = s_testCredentialRight,
+                    TargetName = "HTTP/foo",
+                    RequiredProtectionLevel = ProtectionLevel.Sign
+                });
+
+            DoNtlmExchange(fakeNtlmServer, ntAuth);
+
+            Assert.True(fakeNtlmServer.IsAuthenticated);
+        }
+
         [ConditionalTheory(typeof(NegotiateAuthenticationTests), nameof(IsNtlmAvailable))]
         [InlineData(true, true)]
         [InlineData(true, false)]