diff --git a/src/mcp/server/mcpserver/utilities/func_metadata.py b/src/mcp/server/mcpserver/utilities/func_metadata.py
index 4b539ce1f..0d6b9abc2 100644
--- a/src/mcp/server/mcpserver/utilities/func_metadata.py
+++ b/src/mcp/server/mcpserver/utilities/func_metadata.py
@@ -149,7 +149,7 @@ def pre_parse_json(self, data: dict[str, Any]) -> dict[str, Any]:
                 continue
 
             field_info = key_to_field_info[data_key]
-            if isinstance(data_value, str) and field_info.annotation is not str:
+            if isinstance(data_value, str) and _should_pre_parse_json(field_info.annotation):
                 try:
                     pre_parsed = json.loads(data_value)
                 except json.JSONDecodeError:
@@ -420,6 +420,18 @@ def _try_create_model_and_schema(
 
 _no_default = object()
 
+_SIMPLE_TYPES: frozenset[type] = frozenset({str, int, float, bool, type(None)})
+
+
+def _should_pre_parse_json(annotation: Any) -> bool:
+    """Return True if the annotation requires JSON pre-parsing."""
+    if annotation is str:
+        return False
+    origin = get_origin(annotation)
+    if origin is not None and is_union_origin(origin):
+        return any(arg not in _SIMPLE_TYPES for arg in get_args(annotation))
+    return True
+
 
 def _create_model_from_class(cls: type[Any], type_hints: dict[str, Any]) -> type[BaseModel]:
     """Create a Pydantic model from an ordinary class.
diff --git a/tests/server/mcpserver/test_func_metadata.py b/tests/server/mcpserver/test_func_metadata.py
index c57d1ee9f..ac4881271 100644
--- a/tests/server/mcpserver/test_func_metadata.py
+++ b/tests/server/mcpserver/test_func_metadata.py
@@ -551,6 +551,31 @@ def handle_json_payload(payload: str, strict_mode: bool = False) -> str:
     assert result == f"Handled payload of length {len(json_array_payload)}"
 
 
+def test_str_union_pre_parse_json():
+    """Regression test for #1873: pre_parse_json should not JSON-parse strings
+    when the annotation is a union of simple types like str | None.
+    """
+
+    def func_optional_str(value: str | None = None) -> str:  # pragma: no cover
+        return str(value)
+
+    meta = func_metadata(func_optional_str)
+
+    # str | None: JSON object/array strings should be preserved, not parsed
+    json_obj = '{"database": "postgres", "port": 5432}'
+    assert meta.pre_parse_json({"value": json_obj})["value"] == json_obj
+
+    json_array = '["item1", "item2"]'
+    assert meta.pre_parse_json({"value": json_array})["value"] == json_array
+
+    # Complex unions like list[str] | None should still pre-parse
+    def func_optional_list(items: list[str] | None = None) -> str:  # pragma: no cover
+        return str(items)
+
+    meta_list = func_metadata(func_optional_list)
+    assert meta_list.pre_parse_json({"items": '["a", "b", "c"]'})["items"] == ["a", "b", "c"]
+
+
 # Tests for structured output functionality