diff --git a/src/OptionalValues/OptionalValueJsonExtensions.cs b/src/OptionalValues/OptionalValueJsonExtensions.cs
index 2ef3f5e..24cff3e 100644
--- a/src/OptionalValues/OptionalValueJsonExtensions.cs
+++ b/src/OptionalValues/OptionalValueJsonExtensions.cs
@@ -11,6 +11,7 @@ public static class OptionalValueJsonExtensions
     /// <summary>
     /// Modifies the provided <see cref="JsonSerializerOptions"/> to add support for <see cref="OptionalValue{T}"/>.
     /// </summary>
+    /// <remarks>This should prefereably be done as the last call, as it applies a modifier to the registered <see cref="JsonTypeInfoResolver"/> instances in the TypeInfoResolverChain.</remarks>
     /// <param name="options">The <see cref="JsonSerializerOptions"/> to modify.</param>
     /// <returns>The modified <see cref="JsonSerializerOptions"/> to allow for chaining.</returns>
     /// <exception cref="ArgumentNullException">Thrown when <paramref name="options"/> is <see langword="null"/>.</exception>
@@ -18,8 +19,16 @@ public static JsonSerializerOptions AddOptionalValueSupport(this JsonSerializerO
     {
         ArgumentNullException.ThrowIfNull(options);
 
-        options.TypeInfoResolver = (options.TypeInfoResolver ?? new DefaultJsonTypeInfoResolver())
-            .WithAddedModifier(OptionalValueJsonTypeInfoResolverModifier.ModifyTypeInfo);
+        // If the options do not have a TypeInfoResolver, add the default one, with the modifier.
+        options.TypeInfoResolver ??= new DefaultJsonTypeInfoResolver();
+
+        // We need to add the modifier to all resolvers in the chain,
+        // because it needs to be applied to all types and it's properties.
+        for (var i = 0; i < options.TypeInfoResolverChain.Count; i++)
+        {
+            options.TypeInfoResolverChain[i] = options.TypeInfoResolverChain[i]
+                .WithAddedModifier(OptionalValueJsonTypeInfoResolverModifier.ModifyTypeInfo);
+        }
 
         return options;
     }
@@ -29,7 +38,7 @@ public static JsonSerializerOptions AddOptionalValueSupport(this JsonSerializerO
     /// </summary>
     /// <param name="options">The base <see cref="JsonSerializerOptions"/> options to copy.</param>
     /// <returns>A new <see cref="JsonSerializerOptions"/> based on the provided options with support for <see cref="OptionalValue{T}"/>.</returns>
-    public static JsonSerializerOptions WithOptionalValueSupport(this JsonSerializerOptions options) =>
-        new JsonSerializerOptions(options)
+    public static JsonSerializerOptions WithOptionalValueSupport(this JsonSerializerOptions options)
+        => new JsonSerializerOptions(options)
             .AddOptionalValueSupport();
 }
\ No newline at end of file
diff --git a/test/OptionalValues.Tests/OptionalValueJsonWithSourceGeneratorTest.cs b/test/OptionalValues.Tests/OptionalValueJsonWithSourceGeneratorTest.cs
new file mode 100644
index 0000000..8c90877
--- /dev/null
+++ b/test/OptionalValues.Tests/OptionalValueJsonWithSourceGeneratorTest.cs
@@ -0,0 +1,184 @@
+using System.Text.Json;
+using System.Text.Json.Serialization;
+
+namespace OptionalValues.Tests;
+
+public class OptionalValueJsonWithSourceGeneratorTest
+{
+    private static JsonSerializerOptions CreateOptionsSingleContext()
+    {
+        var options = new JsonSerializerOptions
+        {
+            TypeInfoResolver = OptionalValueJsonWithSourceGeneratorJsonSerializationContext.Default
+        };
+        options.AddOptionalValueSupport();
+        return options;
+    }
+
+    private static JsonSerializerOptions CreateOptionsMultipleContexts()
+    {
+        var options = new JsonSerializerOptions
+        {
+            TypeInfoResolverChain =
+            {
+                OptionalValueJsonWithSourceGeneratorJsonSerializationContext.Default,
+                OtherOptionalValueJsonWithSourceGeneratorJsonSerializationContext.Default
+            }
+        };
+        // This needs to be done last, because it will add modifiers to all resolvers in the chain.
+        options.AddOptionalValueSupport();
+        return options;
+    }
+
+    [Fact]
+    public void SerializeWithValues_ShouldWriteValues()
+    {
+        var model = new TestModel
+        {
+            Name = new OptionalValue<string>("John"),
+            Age = new OptionalValue<int>(42)
+        };
+
+        var options = CreateOptionsSingleContext();
+        var json = JsonSerializer.Serialize(model, options);
+
+        Assert.Equal("""{"Name":"John","Age":42}""", json);
+    }
+
+    [Fact]
+    public void SerializeWithUnspecified_ShouldNotWriteValues()
+    {
+        var model = new TestModel
+        {
+            Name = OptionalValue<string>.Unspecified,
+            Age = OptionalValue<int>.Unspecified
+        };
+
+        var options = CreateOptionsSingleContext();
+        var json = JsonSerializer.Serialize(model, options);
+
+        Assert.Equal("{}", json);
+    }
+
+    [Fact]
+    public void DeserializeWithValues_ShouldReadValues()
+    {
+        var json = """{"Name":"John","Age":42}""";
+
+        var options = CreateOptionsSingleContext();
+        var model = JsonSerializer.Deserialize<TestModel>(json, options);
+
+        Assert.Equal("John", model.Name.Value);
+        Assert.Equal(42, model.Age.Value);
+    }
+
+    [Fact]
+    public void DeserializeWithUnspecified_ShouldReadUnspecified()
+    {
+        var json = "{}";
+
+        var options = CreateOptionsSingleContext();
+        var model = JsonSerializer.Deserialize<TestModel>(json, options);
+
+        Assert.False(model.Name.IsSpecified);
+        Assert.False(model.Age.IsSpecified);
+    }
+
+    [Fact]
+    public void SerializeWithValuesMultipleContexts_ShouldWriteValues()
+    {
+        var model = new TestModelOtherContext
+        {
+            Test = new TestModel
+            {
+                Name = new OptionalValue<string>("John"),
+                Age = new OptionalValue<int>(42)
+            },
+            Street = new OptionalValue<string>("Main Street"),
+            HouseNumber = new OptionalValue<int>(42)
+        };
+
+        var options = CreateOptionsMultipleContexts();
+        var json = JsonSerializer.Serialize(model, options);
+
+        Assert.Equal("""{"Test":{"Name":"John","Age":42},"Street":"Main Street","HouseNumber":42}""", json);
+    }
+
+    [Fact]
+    public void SerializeWithUnspecifiedMultipleContexts_ShouldNotWriteValues()
+    {
+        var model = new TestModelOtherContext
+        {
+            Test = new TestModel
+            {
+                Name = OptionalValue<string>.Unspecified,
+                Age = OptionalValue<int>.Unspecified
+            },
+            Street = OptionalValue<string>.Unspecified,
+            HouseNumber = OptionalValue<int>.Unspecified
+        };
+
+        var options = CreateOptionsMultipleContexts();
+        var json = JsonSerializer.Serialize(model, options);
+
+        Assert.Equal("""{"Test":{}}""", json);
+    }
+
+    [Fact]
+    public void DeserializeWithValuesMultipleContexts_ShouldReadValues()
+    {
+        var json = """{"Test":{"Name":"John","Age":42},"Street":"Main Street","HouseNumber":42}""";
+
+        var options = CreateOptionsMultipleContexts();
+        var model = JsonSerializer.Deserialize<TestModelOtherContext>(json, options);
+
+        Assert.Equal("John", model.Test.Value.Name.Value);
+        Assert.Equal(42, model.Test.Value.Age.Value);
+        Assert.Equal("Main Street", model.Street.Value);
+        Assert.Equal(42, model.HouseNumber.Value);
+    }
+
+    [Fact]
+    public void DeserializeWithUnspecifiedMultipleContexts_ShouldReadUnspecified()
+    {
+        var json = """{"Test":{}}""";
+
+        var options = CreateOptionsMultipleContexts();
+        var model = JsonSerializer.Deserialize<TestModelOtherContext>(json, options);
+
+        Assert.True(model.Test.IsSpecified);
+
+        Assert.False(model.Test.SpecifiedValue.Name.IsSpecified);
+        Assert.False(model.Test.SpecifiedValue.Age.IsSpecified);
+        Assert.False(model.Street.IsSpecified);
+        Assert.False(model.HouseNumber.IsSpecified);
+    }
+
+    public class TestModel
+    {
+        public OptionalValue<string> Name { get; set; }
+
+        public OptionalValue<int> Age { get; set; }
+    }
+
+    public class TestModelOtherContext
+    {
+        public OptionalValue<TestModel> Test { get; set; }
+
+        public OptionalValue<string> Street { get; set; }
+
+        public OptionalValue<int> HouseNumber { get; set; }
+    }
+}
+
+[JsonSerializable(typeof(OptionalValueJsonWithSourceGeneratorTest.TestModel))]
+[JsonSerializable(typeof(int))]
+[JsonSerializable(typeof(string))]
+public partial class OptionalValueJsonWithSourceGeneratorJsonSerializationContext : JsonSerializerContext
+{
+}
+
+[JsonSerializable(typeof(OptionalValueJsonWithSourceGeneratorTest.TestModelOtherContext))]
+public partial class OtherOptionalValueJsonWithSourceGeneratorJsonSerializationContext : JsonSerializerContext
+{
+}
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