diff --git a/src/Microsoft.OData.Core/Json/ODataJsonPropertySerializer.cs b/src/Microsoft.OData.Core/Json/ODataJsonPropertySerializer.cs
index 71c34dab4e..bf5399978b 100644
--- a/src/Microsoft.OData.Core/Json/ODataJsonPropertySerializer.cs
+++ b/src/Microsoft.OData.Core/Json/ODataJsonPropertySerializer.cs
@@ -388,7 +388,9 @@ await WriteStreamValueAsync(streamReferenceValue, property.Name, metadataBuilder
                 return;
             }
 
-            if (value is ODataNullValue || value == null)
+            if (value is ODataNullValue
+                || value == null
+                || value is ODataJsonElementValue jsonElement && jsonElement.Value.ValueKind == System.Text.Json.JsonValueKind.Null)
             {
                 await this.WriteNullPropertyAsync(property).ConfigureAwait(false);
                 return;
diff --git a/src/Microsoft.OData.Core/ODataContextUrlInfo.cs b/src/Microsoft.OData.Core/ODataContextUrlInfo.cs
index da4c2ff6ce..7ee8f06119 100644
--- a/src/Microsoft.OData.Core/ODataContextUrlInfo.cs
+++ b/src/Microsoft.OData.Core/ODataContextUrlInfo.cs
@@ -17,6 +17,7 @@ namespace Microsoft.OData
     using Microsoft.OData.UriParser;
     using Microsoft.OData.Edm;
     using Microsoft.OData.Core;
+    using System.Text.Json;
     #endregion Namespaces
 
     /// <summary>
@@ -454,22 +455,35 @@ private static string GetTypeNameForValue(ODataValue value, IEdmModel model)
                 return ODataConstants.ContextUriFragmentUntyped;
             }
 
-            ODataPrimitiveValue primitive = value as ODataPrimitiveValue;
-            if (primitive == null)
+            if (value is ODataPrimitiveValue primitive)
             {
-                Debug.Assert(value is ODataStreamReferenceValue, "value is ODataStreamReferenceValue");
-                throw new ODataException(SRResources.ODataContextUriBuilder_StreamValueMustBePropertiesOfODataResource);
+
+                // Try convert to underlying type if the primitive value is unsigned int.
+                IEdmTypeDefinitionReference typeDefinitionReference = model.ResolveUIntTypeDefinition(primitive.Value);
+                if (typeDefinitionReference != null)
+                {
+                    return typeDefinitionReference.FullName();
+                }
+
+                IEdmPrimitiveTypeReference primitiveValueTypeReference = EdmLibraryExtensions.GetPrimitiveTypeReference(primitive.Value.GetType());
+                return primitiveValueTypeReference == null ? null : primitiveValueTypeReference.FullName();
             }
 
-            // Try convert to underlying type if the primitive value is unsigned int.
-            IEdmTypeDefinitionReference typeDefinitionReference = model.ResolveUIntTypeDefinition(primitive.Value);
-            if (typeDefinitionReference != null)
+            if (value is ODataJsonElementValue jsonElementValue)
             {
-                return typeDefinitionReference.FullName();
-            }
+                JsonElement jsonElement = jsonElementValue.Value;
+                return jsonElement.ValueKind switch
+                {
+                    JsonValueKind.True or JsonValueKind.False => EdmCoreModel.Instance.GetPrimitive(EdmPrimitiveTypeKind.Boolean, true).FullName(),
+                    JsonValueKind.Number => EdmCoreModel.Instance.GetPrimitive(EdmPrimitiveTypeKind.Double, true).FullName(),
+                    JsonValueKind.String => EdmCoreModel.Instance.GetPrimitive(EdmPrimitiveTypeKind.String, true).FullName(),
+                    JsonValueKind.Null => ODataConstants.ContextUriFragmentNull,
+                    _ => ODataConstants.ContextUriFragmentUntyped
+                };
+            };
 
-            IEdmPrimitiveTypeReference primitiveValueTypeReference = EdmLibraryExtensions.GetPrimitiveTypeReference(primitive.Value.GetType());
-            return primitiveValueTypeReference == null ? null : primitiveValueTypeReference.FullName();
+            Debug.Assert(value is ODataStreamReferenceValue, "value is ODataStreamReferenceValue");
+            throw new ODataException(SRResources.ODataContextUriBuilder_StreamValueMustBePropertiesOfODataResource);
         }
 
         private static string CreateApplyUriSegment(ApplyClause applyClause)
diff --git a/test/UnitTests/Microsoft.OData.Core.Tests/ODataMessageWriterTests.cs b/test/UnitTests/Microsoft.OData.Core.Tests/ODataMessageWriterTests.cs
index 489ac46852..f5378d4330 100644
--- a/test/UnitTests/Microsoft.OData.Core.Tests/ODataMessageWriterTests.cs
+++ b/test/UnitTests/Microsoft.OData.Core.Tests/ODataMessageWriterTests.cs
@@ -19,6 +19,7 @@
 using Microsoft.OData.Edm.Csdl;
 using Xunit;
 using Microsoft.OData.Core;
+using System.Reflection.Metadata;
 
 namespace Microsoft.OData.Tests
 {
@@ -309,6 +310,113 @@ public async Task SupportsODataUtf8JsonWriterAsync()
             Assert.Equal("{\"@odata.context\":\"http://www.example.com/$metadata#Edm.String\",\"value\":\"This is a test ия\"}", output);
         }
 
+        [Theory]
+        [InlineData("true", "Edm.Boolean")]
+        [InlineData("false", "Edm.Boolean")]
+        [InlineData("123", "Edm.Double")]
+        [InlineData("\"This is a string\"", "Edm.String")]
+        public async Task SupportsTopLevelPropertyWithPrimitiveJsonElementValueAsync(string rawValue, string expectedType)
+        {
+            // Arrange
+            EdmModel model = new EdmModel();
+            JsonElement jsonElement = JsonDocument.Parse(rawValue).RootElement;
+
+            // Act
+            string output = await WriteAndGetPayloadAsync(
+                model,
+                "application/json",
+                (writer) => writer.WritePropertyAsync(new ODataProperty()
+                {
+                    Name = "Name",
+                    Value = new ODataJsonElementValue(jsonElement)
+                }),
+                configureServices: (containerBuilder) =>
+                {
+                    containerBuilder.AddSingleton<IJsonWriterFactory>(sp => ODataUtf8JsonWriterFactory.Default);
+                });
+
+            // Assert
+            Assert.Equal($"{{\"@odata.context\":\"http://www.example.com/$metadata#{expectedType}\",\"value\":{rawValue}}}", output);
+        }
+
+        [Theory]
+        [InlineData("[1,2,3]")]
+        [InlineData("{\"foo\":\"bar\"}")]
+        public async Task WritesUntypedContextJsonElementTopLevelPropertyWithArrayOrObject(string rawValue)
+        {
+            // Arrange
+            EdmModel model = new EdmModel();
+            JsonElement jsonElement = JsonDocument.Parse(rawValue).RootElement;
+
+            // Act
+            string output = await WriteAndGetPayloadAsync(
+                model,
+                "application/json",
+                (writer) => writer.WritePropertyAsync(new ODataProperty()
+                {
+                    Name = "Name",
+                    Value = new ODataJsonElementValue(jsonElement)
+                }),
+                configureServices: (containerBuilder) =>
+                {
+                    containerBuilder.AddSingleton<IJsonWriterFactory>(sp => ODataUtf8JsonWriterFactory.Default);
+                });
+
+            // Assert
+            Assert.Equal($"{{\"@odata.context\":\"http://www.example.com/$metadata#Edm.Untyped\",\"value\":{rawValue}}}", output);
+        }
+
+        [Theory]
+        [InlineData(true, "Edm.Boolean")]
+        [InlineData(false, "Edm.Boolean")]
+        [InlineData(123, "Edm.Int32")]
+        [InlineData(123.0, "Edm.Double")]
+        [InlineData("\"This is a string\"", "Edm.String")]
+        public async Task SupportsTopLevelPropertyWithPrimitiveValueAsync(object value, string expectedType)
+        {
+            // Arrange
+            EdmModel model = new EdmModel();
+
+            // Act
+            string output = await WriteAndGetPayloadAsync(
+                model,
+                "application/json",
+                (writer) => writer.WritePropertyAsync(new ODataProperty()
+                {
+                    Name = "Name",
+                    Value = value
+                }),
+                configureServices: (containerBuilder) =>
+                {
+                    containerBuilder.AddSingleton<IJsonWriterFactory>(sp => ODataUtf8JsonWriterFactory.Default);
+                });
+
+            // Assert
+            Assert.Equal($"{{\"@odata.context\":\"http://www.example.com/$metadata#{expectedType}\",\"value\":{value}}}", output);
+        }
+
+        [Fact]
+        public async Task ThrowsExceptionIfJsonElementValueContainsNullInTopLevelPropertyAsync()
+        {
+            // Arrange
+            EdmModel model = new EdmModel();
+            JsonElement jsonElement = JsonDocument.Parse("null").RootElement;
+
+            // Act
+            var testCode = async () => await WriteAndGetPayloadAsync(
+                model,
+                "application/json",
+                (writer) => writer.WritePropertyAsync(new ODataProperty()
+                {
+                    Name = "Name",
+                    Value = new ODataJsonElementValue(jsonElement)
+                }));
+
+            // Assert
+            var exception = await Assert.ThrowsAsync<ODataException>(testCode);
+            Assert.Equal("Cannot write the value 'null' in top level property; return 204 instead.", exception.Message);
+        }
+
         [Theory]
         [InlineData("utf-8")]
         [InlineData("utf-16")]