diff --git a/src/fastmcp/experimental/utilities/openapi/schemas.py b/src/fastmcp/experimental/utilities/openapi/schemas.py
index 7ccc182ca..c7ea71f58 100644
--- a/src/fastmcp/experimental/utilities/openapi/schemas.py
+++ b/src/fastmcp/experimental/utilities/openapi/schemas.py
@@ -199,6 +199,86 @@ def _make_optional_parameter_nullable(schema: dict[str, Any]) -> dict[str, Any]:
     return schema
 
 
+def _add_null_to_type(schema: dict[str, Any]) -> None:
+    """Add 'null' to the schema's type field or handle oneOf/anyOf/allOf constructs if not already present."""
+    if "type" in schema:
+        current_type = schema["type"]
+
+        if isinstance(current_type, str):
+            # Convert string type to array with null
+            schema["type"] = [current_type, "null"]
+        elif isinstance(current_type, list):
+            # Add null to array if not already present
+            if "null" not in current_type:
+                schema["type"] = current_type + ["null"]
+    elif "oneOf" in schema:
+        # Convert oneOf to anyOf with null type
+        schema["anyOf"] = schema.pop("oneOf") + [{"type": "null"}]
+    elif "anyOf" in schema:
+        # Add null type to anyOf if not already present
+        if not any(item.get("type") == "null" for item in schema["anyOf"]):
+            schema["anyOf"].append({"type": "null"})
+    elif "allOf" in schema:
+        # For allOf, wrap in anyOf with null - this means (all conditions) OR null
+        schema["anyOf"] = [{"allOf": schema.pop("allOf")}, {"type": "null"}]
+
+
+def _handle_nullable_fields(schema: dict[str, Any] | Any) -> dict[str, Any] | Any:
+    """Convert OpenAPI nullable fields to JSON Schema format: {"type": "string",
+    "nullable": true} -> {"type": ["string", "null"]}"""
+
+    if not isinstance(schema, dict):
+        return schema
+
+    # Check if we need to modify anything first to avoid unnecessary copying
+    has_root_nullable_field = "nullable" in schema
+    has_root_nullable_true = (
+        has_root_nullable_field
+        and schema["nullable"]
+        and (
+            "type" in schema
+            or "oneOf" in schema
+            or "anyOf" in schema
+            or "allOf" in schema
+        )
+    )
+
+    has_property_nullable_field = False
+    if "properties" in schema:
+        for prop_schema in schema["properties"].values():
+            if isinstance(prop_schema, dict) and "nullable" in prop_schema:
+                has_property_nullable_field = True
+                break
+
+    # If no nullable fields at all, return original schema unchanged
+    if not has_root_nullable_field and not has_property_nullable_field:
+        return schema
+
+    # Only copy if we need to modify
+    result = schema.copy()
+
+    # Handle root level nullable - always remove the field, convert type if true
+    if has_root_nullable_field:
+        result.pop("nullable")
+        if has_root_nullable_true:
+            _add_null_to_type(result)
+
+    # Handle properties nullable fields
+    if has_property_nullable_field and "properties" in result:
+        for prop_name, prop_schema in result["properties"].items():
+            if isinstance(prop_schema, dict) and "nullable" in prop_schema:
+                nullable_value = prop_schema.pop("nullable")
+                if nullable_value and (
+                    "type" in prop_schema
+                    or "oneOf" in prop_schema
+                    or "anyOf" in prop_schema
+                    or "allOf" in prop_schema
+                ):
+                    _add_null_to_type(prop_schema)
+
+    return result
+
+
 def _combine_schemas_and_map_params(
     route: HTTPRoute,
 ) -> tuple[dict[str, Any], dict[str, dict[str, str]]]:
@@ -499,6 +579,19 @@ def extract_output_schema_from_responses(
     # Clean and copy the schema
     output_schema = schema.copy()
 
+    # If schema has a $ref, resolve it first before processing nullable fields
+    if "$ref" in output_schema and schema_definitions:
+        ref_path = output_schema["$ref"]
+        if ref_path.startswith("#/components/schemas/"):
+            schema_name = ref_path.split("/")[-1]
+            if schema_name in schema_definitions:
+                # Replace $ref with the actual schema definition
+                output_schema = schema_definitions[schema_name].copy()
+
+    # Handle OpenAPI nullable fields by converting them to JSON Schema format
+    # This prevents "None is not of type 'string'" validation errors
+    output_schema = _handle_nullable_fields(output_schema)
+
     # MCP requires output schemas to be objects. If this schema is not an object,
     # we need to wrap it similar to how ParsedFunction.from_function() does it
     if output_schema.get("type") != "object":
@@ -511,9 +604,13 @@ def extract_output_schema_from_responses(
         }
         output_schema = wrapped_schema
 
-    # Add schema definitions if available
-    if schema_definitions:
-        output_schema["$defs"] = schema_definitions.copy()
+    # Add schema definitions if available and handle nullable fields in them
+    # Only add $defs if we didn't resolve the $ref inline above
+    if schema_definitions and "$ref" not in schema.copy():
+        processed_defs = {}
+        for def_name, def_schema in schema_definitions.items():
+            processed_defs[def_name] = _handle_nullable_fields(def_schema)
+        output_schema["$defs"] = processed_defs
 
     # Use lightweight compression - prune additionalProperties and unused definitions
     if output_schema.get("additionalProperties") is False:
@@ -564,5 +661,6 @@ __all__ = [
     "extract_output_schema_from_responses",
     "_replace_ref_with_defs",
     "_make_optional_parameter_nullable",
+    "_handle_nullable_fields",
     "_adjust_union_types",
 ]
diff --git a/src/fastmcp/utilities/openapi.py b/src/fastmcp/utilities/openapi.py
index ef7ae874f..121dd7249 100644
--- a/src/fastmcp/utilities/openapi.py
+++ b/src/fastmcp/utilities/openapi.py
@@ -187,6 +187,7 @@ __all__ = [
     "parse_openapi_to_http_routes",
     "extract_output_schema_from_responses",
     "format_deep_object_parameter",
+    "_handle_nullable_fields",
 ]
 
 # Type variables for generic parser
@@ -1169,6 +1170,86 @@ def _make_optional_parameter_nullable(schema: dict[str, Any]) -> dict[str, Any]:
     return schema
 
 
+def _add_null_to_type(schema: dict[str, Any]) -> None:
+    """Add 'null' to the schema's type field or handle oneOf/anyOf/allOf constructs if not already present."""
+    if "type" in schema:
+        current_type = schema["type"]
+
+        if isinstance(current_type, str):
+            # Convert string type to array with null
+            schema["type"] = [current_type, "null"]
+        elif isinstance(current_type, list):
+            # Add null to array if not already present
+            if "null" not in current_type:
+                schema["type"] = current_type + ["null"]
+    elif "oneOf" in schema:
+        # Convert oneOf to anyOf with null type
+        schema["anyOf"] = schema.pop("oneOf") + [{"type": "null"}]
+    elif "anyOf" in schema:
+        # Add null type to anyOf if not already present
+        if not any(item.get("type") == "null" for item in schema["anyOf"]):
+            schema["anyOf"].append({"type": "null"})
+    elif "allOf" in schema:
+        # For allOf, wrap in anyOf with null - this means (all conditions) OR null
+        schema["anyOf"] = [{"allOf": schema.pop("allOf")}, {"type": "null"}]
+
+
+def _handle_nullable_fields(schema: dict[str, Any] | Any) -> dict[str, Any] | Any:
+    """Convert OpenAPI nullable fields to JSON Schema format: {"type": "string",
+    "nullable": true} -> {"type": ["string", "null"]}"""
+
+    if not isinstance(schema, dict):
+        return schema
+
+    # Check if we need to modify anything first to avoid unnecessary copying
+    has_root_nullable_field = "nullable" in schema
+    has_root_nullable_true = (
+        has_root_nullable_field
+        and schema["nullable"]
+        and (
+            "type" in schema
+            or "oneOf" in schema
+            or "anyOf" in schema
+            or "allOf" in schema
+        )
+    )
+
+    has_property_nullable_field = False
+    if "properties" in schema:
+        for prop_schema in schema["properties"].values():
+            if isinstance(prop_schema, dict) and "nullable" in prop_schema:
+                has_property_nullable_field = True
+                break
+
+    # If no nullable fields at all, return original schema unchanged
+    if not has_root_nullable_field and not has_property_nullable_field:
+        return schema
+
+    # Only copy if we need to modify
+    result = schema.copy()
+
+    # Handle root level nullable - always remove the field, convert type if true
+    if has_root_nullable_field:
+        result.pop("nullable")
+        if has_root_nullable_true:
+            _add_null_to_type(result)
+
+    # Handle properties nullable fields
+    if has_property_nullable_field and "properties" in result:
+        for prop_name, prop_schema in result["properties"].items():
+            if isinstance(prop_schema, dict) and "nullable" in prop_schema:
+                nullable_value = prop_schema.pop("nullable")
+                if nullable_value and (
+                    "type" in prop_schema
+                    or "oneOf" in prop_schema
+                    or "anyOf" in prop_schema
+                    or "allOf" in prop_schema
+                ):
+                    _add_null_to_type(prop_schema)
+
+    return result
+
+
 def _combine_schemas(route: HTTPRoute) -> dict[str, Any]:
     """
     Combines parameter and request body schemas into a single schema.
@@ -1388,6 +1469,19 @@ def extract_output_schema_from_responses(
     # Clean and copy the schema
     output_schema = schema.copy()
 
+    # If schema has a $ref, resolve it first before processing nullable fields
+    if "$ref" in output_schema and schema_definitions:
+        ref_path = output_schema["$ref"]
+        if ref_path.startswith("#/components/schemas/"):
+            schema_name = ref_path.split("/")[-1]
+            if schema_name in schema_definitions:
+                # Replace $ref with the actual schema definition
+                output_schema = schema_definitions[schema_name].copy()
+
+    # Handle OpenAPI nullable fields by converting them to JSON Schema format
+    # This prevents "None is not of type 'string'" validation errors
+    output_schema = _handle_nullable_fields(output_schema)
+
     # MCP requires output schemas to be objects. If this schema is not an object,
     # we need to wrap it similar to how ParsedFunction.from_function() does it
     if output_schema.get("type") != "object":
@@ -1400,9 +1494,13 @@ def extract_output_schema_from_responses(
         }
         output_schema = wrapped_schema
 
-    # Add schema definitions if available
-    if schema_definitions:
-        output_schema["$defs"] = schema_definitions.copy()
+    # Add schema definitions if available and handle nullable fields in them
+    # Only add $defs if we didn't resolve the $ref inline above
+    if schema_definitions and "$ref" not in schema.copy():
+        processed_defs = {}
+        for def_name, def_schema in schema_definitions.items():
+            processed_defs[def_name] = _handle_nullable_fields(def_schema)
+        output_schema["$defs"] = processed_defs
 
     # Use lightweight compression - prune additionalProperties and unused definitions
     if output_schema.get("additionalProperties") is False:
diff --git a/tests/experimental/utilities/openapi/test_nullable_fields.py b/tests/experimental/utilities/openapi/test_nullable_fields.py
new file mode 100644
index 000000000..9f8d185d6
--- /dev/null
+++ b/tests/experimental/utilities/openapi/test_nullable_fields.py
@@ -0,0 +1,243 @@
+"""Tests for nullable field handling in OpenAPI schemas."""
+
+from fastmcp.experimental.utilities.openapi.schemas import _handle_nullable_fields
+
+
+class TestHandleNullableFields:
+    """Test conversion of OpenAPI nullable fields to JSON Schema format."""
+
+    def test_root_level_nullable_string(self):
+        """Test nullable string at root level."""
+        input_schema = {"type": "string", "nullable": True}
+        expected = {"type": ["string", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_root_level_nullable_integer(self):
+        """Test nullable integer at root level."""
+        input_schema = {"type": "integer", "nullable": True}
+        expected = {"type": ["integer", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_root_level_nullable_boolean(self):
+        """Test nullable boolean at root level."""
+        input_schema = {"type": "boolean", "nullable": True}
+        expected = {"type": ["boolean", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_property_level_nullable_fields(self):
+        """Test nullable fields in properties."""
+        input_schema = {
+            "type": "object",
+            "properties": {
+                "name": {"type": "string"},
+                "company": {"type": "string", "nullable": True},
+                "age": {"type": "integer", "nullable": True},
+                "active": {"type": "boolean", "nullable": True},
+            },
+        }
+        expected = {
+            "type": "object",
+            "properties": {
+                "name": {"type": "string"},
+                "company": {"type": ["string", "null"]},
+                "age": {"type": ["integer", "null"]},
+                "active": {"type": ["boolean", "null"]},
+            },
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_mixed_nullable_and_non_nullable(self):
+        """Test mix of nullable and non-nullable fields."""
+        input_schema = {
+            "type": "object",
+            "properties": {
+                "required_field": {"type": "string"},
+                "optional_nullable": {"type": "string", "nullable": True},
+                "optional_non_nullable": {"type": "string"},
+            },
+            "required": ["required_field"],
+        }
+        expected = {
+            "type": "object",
+            "properties": {
+                "required_field": {"type": "string"},
+                "optional_nullable": {"type": ["string", "null"]},
+                "optional_non_nullable": {"type": "string"},
+            },
+            "required": ["required_field"],
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_nullable_false_ignored(self):
+        """Test that nullable: false is ignored (removed but no type change)."""
+        input_schema = {"type": "string", "nullable": False}
+        expected = {"type": "string"}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_no_nullable_field_unchanged(self):
+        """Test that schemas without nullable field are unchanged."""
+        input_schema = {
+            "type": "object",
+            "properties": {"name": {"type": "string"}},
+        }
+        expected = input_schema.copy()
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_nullable_without_type_removes_nullable(self):
+        """Test that nullable field is removed even without type."""
+        input_schema = {"nullable": True, "description": "Some field"}
+        expected = {"description": "Some field"}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_preserves_other_fields(self):
+        """Test that other fields are preserved during conversion."""
+        input_schema = {
+            "type": "string",
+            "nullable": True,
+            "description": "A nullable string",
+            "example": "test",
+            "format": "email",
+        }
+        expected = {
+            "type": ["string", "null"],
+            "description": "A nullable string",
+            "example": "test",
+            "format": "email",
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_non_dict_input_unchanged(self):
+        """Test that non-dict inputs are returned unchanged."""
+        assert _handle_nullable_fields("string") == "string"  # type: ignore[arg-type]
+        assert _handle_nullable_fields(123) == 123  # type: ignore[arg-type]
+        assert _handle_nullable_fields(None) is None  # type: ignore[arg-type]
+        assert _handle_nullable_fields([1, 2, 3]) == [1, 2, 3]  # type: ignore[arg-type]
+
+    def test_performance_optimization_no_copy_when_unchanged(self):
+        """Test that schemas without nullable fields return the same object (no copy)."""
+        input_schema = {
+            "type": "object",
+            "properties": {"name": {"type": "string"}},
+        }
+        result = _handle_nullable_fields(input_schema)
+        # Should return the exact same object, not a copy
+        assert result is input_schema
+
+    def test_union_types_with_nullable(self):
+        """Test nullable handling with existing union types (type as array)."""
+        input_schema = {"type": ["string", "integer"], "nullable": True}
+        expected = {"type": ["string", "integer", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_already_nullable_union_unchanged(self):
+        """Test that union types already containing null are not modified."""
+        input_schema = {"type": ["string", "null"], "nullable": True}
+        expected = {"type": ["string", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_property_level_union_with_nullable(self):
+        """Test nullable handling with union types in properties."""
+        input_schema = {
+            "type": "object",
+            "properties": {"value": {"type": ["string", "integer"], "nullable": True}},
+        }
+        expected = {
+            "type": "object",
+            "properties": {"value": {"type": ["string", "integer", "null"]}},
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_complex_union_nullable_scenarios(self):
+        """Test various complex union type scenarios."""
+        # Already has null in different position
+        input1 = {"type": ["null", "string", "integer"], "nullable": True}
+        result1 = _handle_nullable_fields(input1)
+        assert result1 == {"type": ["null", "string", "integer"]}
+
+        # Single item array
+        input2 = {"type": ["string"], "nullable": True}
+        result2 = _handle_nullable_fields(input2)
+        assert result2 == {"type": ["string", "null"]}
+
+    def test_oneof_with_nullable(self):
+        """Test nullable handling with oneOf constructs."""
+        input_schema = {
+            "oneOf": [{"type": "string"}, {"type": "integer"}],
+            "nullable": True,
+        }
+        expected = {
+            "anyOf": [{"type": "string"}, {"type": "integer"}, {"type": "null"}]
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_anyof_with_nullable(self):
+        """Test nullable handling with anyOf constructs."""
+        input_schema = {
+            "anyOf": [{"type": "string"}, {"type": "integer"}],
+            "nullable": True,
+        }
+        expected = {
+            "anyOf": [{"type": "string"}, {"type": "integer"}, {"type": "null"}]
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_anyof_already_nullable(self):
+        """Test anyOf that already contains null type."""
+        input_schema = {
+            "anyOf": [{"type": "string"}, {"type": "null"}],
+            "nullable": True,
+        }
+        expected = {"anyOf": [{"type": "string"}, {"type": "null"}]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_allof_with_nullable(self):
+        """Test nullable handling with allOf constructs."""
+        input_schema = {
+            "allOf": [{"type": "string"}, {"minLength": 1}],
+            "nullable": True,
+        }
+        expected = {
+            "anyOf": [
+                {"allOf": [{"type": "string"}, {"minLength": 1}]},
+                {"type": "null"},
+            ]
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_property_level_oneof_with_nullable(self):
+        """Test nullable handling with oneOf in properties."""
+        input_schema = {
+            "type": "object",
+            "properties": {
+                "value": {
+                    "oneOf": [{"type": "string"}, {"type": "integer"}],
+                    "nullable": True,
+                }
+            },
+        }
+        expected = {
+            "type": "object",
+            "properties": {
+                "value": {
+                    "anyOf": [{"type": "string"}, {"type": "integer"}, {"type": "null"}]
+                }
+            },
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
diff --git a/tests/utilities/openapi/test_nullable_fields.py b/tests/utilities/openapi/test_nullable_fields.py
new file mode 100644
index 000000000..1802e1a5d
--- /dev/null
+++ b/tests/utilities/openapi/test_nullable_fields.py
@@ -0,0 +1,243 @@
+"""Tests for nullable field handling in OpenAPI schemas."""
+
+from fastmcp.utilities.openapi import _handle_nullable_fields
+
+
+class TestHandleNullableFields:
+    """Test conversion of OpenAPI nullable fields to JSON Schema format."""
+
+    def test_root_level_nullable_string(self):
+        """Test nullable string at root level."""
+        input_schema = {"type": "string", "nullable": True}
+        expected = {"type": ["string", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_root_level_nullable_integer(self):
+        """Test nullable integer at root level."""
+        input_schema = {"type": "integer", "nullable": True}
+        expected = {"type": ["integer", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_root_level_nullable_boolean(self):
+        """Test nullable boolean at root level."""
+        input_schema = {"type": "boolean", "nullable": True}
+        expected = {"type": ["boolean", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_property_level_nullable_fields(self):
+        """Test nullable fields in properties."""
+        input_schema = {
+            "type": "object",
+            "properties": {
+                "name": {"type": "string"},
+                "company": {"type": "string", "nullable": True},
+                "age": {"type": "integer", "nullable": True},
+                "active": {"type": "boolean", "nullable": True},
+            },
+        }
+        expected = {
+            "type": "object",
+            "properties": {
+                "name": {"type": "string"},
+                "company": {"type": ["string", "null"]},
+                "age": {"type": ["integer", "null"]},
+                "active": {"type": ["boolean", "null"]},
+            },
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_mixed_nullable_and_non_nullable(self):
+        """Test mix of nullable and non-nullable fields."""
+        input_schema = {
+            "type": "object",
+            "properties": {
+                "required_field": {"type": "string"},
+                "optional_nullable": {"type": "string", "nullable": True},
+                "optional_non_nullable": {"type": "string"},
+            },
+            "required": ["required_field"],
+        }
+        expected = {
+            "type": "object",
+            "properties": {
+                "required_field": {"type": "string"},
+                "optional_nullable": {"type": ["string", "null"]},
+                "optional_non_nullable": {"type": "string"},
+            },
+            "required": ["required_field"],
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_nullable_false_ignored(self):
+        """Test that nullable: false is ignored (removed but no type change)."""
+        input_schema = {"type": "string", "nullable": False}
+        expected = {"type": "string"}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_no_nullable_field_unchanged(self):
+        """Test that schemas without nullable field are unchanged."""
+        input_schema = {
+            "type": "object",
+            "properties": {"name": {"type": "string"}},
+        }
+        expected = input_schema.copy()
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_nullable_without_type_removes_nullable(self):
+        """Test that nullable field is removed even without type."""
+        input_schema = {"nullable": True, "description": "Some field"}
+        expected = {"description": "Some field"}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_preserves_other_fields(self):
+        """Test that other fields are preserved during conversion."""
+        input_schema = {
+            "type": "string",
+            "nullable": True,
+            "description": "A nullable string",
+            "example": "test",
+            "format": "email",
+        }
+        expected = {
+            "type": ["string", "null"],
+            "description": "A nullable string",
+            "example": "test",
+            "format": "email",
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_non_dict_input_unchanged(self):
+        """Test that non-dict inputs are returned unchanged."""
+        assert _handle_nullable_fields("string") == "string"  # type: ignore[arg-type]
+        assert _handle_nullable_fields(123) == 123  # type: ignore[arg-type]
+        assert _handle_nullable_fields(None) is None  # type: ignore[arg-type]
+        assert _handle_nullable_fields([1, 2, 3]) == [1, 2, 3]  # type: ignore[arg-type]
+
+    def test_performance_optimization_no_copy_when_unchanged(self):
+        """Test that schemas without nullable fields return the same object (no copy)."""
+        input_schema = {
+            "type": "object",
+            "properties": {"name": {"type": "string"}},
+        }
+        result = _handle_nullable_fields(input_schema)
+        # Should return the exact same object, not a copy
+        assert result is input_schema
+
+    def test_union_types_with_nullable(self):
+        """Test nullable handling with existing union types (type as array)."""
+        input_schema = {"type": ["string", "integer"], "nullable": True}
+        expected = {"type": ["string", "integer", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_already_nullable_union_unchanged(self):
+        """Test that union types already containing null are not modified."""
+        input_schema = {"type": ["string", "null"], "nullable": True}
+        expected = {"type": ["string", "null"]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_property_level_union_with_nullable(self):
+        """Test nullable handling with union types in properties."""
+        input_schema = {
+            "type": "object",
+            "properties": {"value": {"type": ["string", "integer"], "nullable": True}},
+        }
+        expected = {
+            "type": "object",
+            "properties": {"value": {"type": ["string", "integer", "null"]}},
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_complex_union_nullable_scenarios(self):
+        """Test various complex union type scenarios."""
+        # Already has null in different position
+        input1 = {"type": ["null", "string", "integer"], "nullable": True}
+        result1 = _handle_nullable_fields(input1)
+        assert result1 == {"type": ["null", "string", "integer"]}
+
+        # Single item array
+        input2 = {"type": ["string"], "nullable": True}
+        result2 = _handle_nullable_fields(input2)
+        assert result2 == {"type": ["string", "null"]}
+
+    def test_oneof_with_nullable(self):
+        """Test nullable handling with oneOf constructs."""
+        input_schema = {
+            "oneOf": [{"type": "string"}, {"type": "integer"}],
+            "nullable": True,
+        }
+        expected = {
+            "anyOf": [{"type": "string"}, {"type": "integer"}, {"type": "null"}]
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_anyof_with_nullable(self):
+        """Test nullable handling with anyOf constructs."""
+        input_schema = {
+            "anyOf": [{"type": "string"}, {"type": "integer"}],
+            "nullable": True,
+        }
+        expected = {
+            "anyOf": [{"type": "string"}, {"type": "integer"}, {"type": "null"}]
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_anyof_already_nullable(self):
+        """Test anyOf that already contains null type."""
+        input_schema = {
+            "anyOf": [{"type": "string"}, {"type": "null"}],
+            "nullable": True,
+        }
+        expected = {"anyOf": [{"type": "string"}, {"type": "null"}]}
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_allof_with_nullable(self):
+        """Test nullable handling with allOf constructs."""
+        input_schema = {
+            "allOf": [{"type": "string"}, {"minLength": 1}],
+            "nullable": True,
+        }
+        expected = {
+            "anyOf": [
+                {"allOf": [{"type": "string"}, {"minLength": 1}]},
+                {"type": "null"},
+            ]
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected
+
+    def test_property_level_oneof_with_nullable(self):
+        """Test nullable handling with oneOf in properties."""
+        input_schema = {
+            "type": "object",
+            "properties": {
+                "value": {
+                    "oneOf": [{"type": "string"}, {"type": "integer"}],
+                    "nullable": True,
+                }
+            },
+        }
+        expected = {
+            "type": "object",
+            "properties": {
+                "value": {
+                    "anyOf": [{"type": "string"}, {"type": "integer"}, {"type": "null"}]
+                }
+            },
+        }
+        result = _handle_nullable_fields(input_schema)
+        assert result == expected