diff --git a/src/fastmcp/tools/tool.py b/src/fastmcp/tools/tool.py
index eab2df209..bb0c8afd5 100644
--- a/src/fastmcp/tools/tool.py
+++ b/src/fastmcp/tools/tool.py
@@ -8,7 +8,6 @@ from typing import (
     Annotated,
     Any,
     Generic,
-    Literal,
     TypeVar,
     get_type_hints,
 )
@@ -163,7 +162,7 @@ class Tool(FastMCPComponent):
         tags: set[str] | None = None,
         annotations: ToolAnnotations | None = None,
         exclude_args: list[str] | None = None,
-        output_schema: dict[str, Any] | None | NotSetT | Literal[False] = NotSet,
+        output_schema: dict[str, Any] | None | NotSetT = NotSet,
         serializer: Callable[[Any], str] | None = None,
         meta: dict[str, Any] | None = None,
         enabled: bool | None = None,
@@ -199,17 +198,18 @@ class Tool(FastMCPComponent):
     def from_tool(
         cls,
         tool: Tool,
-        transform_fn: Callable[..., Any] | None = None,
+        *,
         name: str | None = None,
         title: str | None | NotSetT = NotSet,
-        transform_args: dict[str, ArgTransform] | None = None,
         description: str | None | NotSetT = NotSet,
         tags: set[str] | None = None,
-        annotations: ToolAnnotations | None = None,
-        output_schema: dict[str, Any] | None | Literal[False] = None,
+        annotations: ToolAnnotations | None | NotSetT = NotSet,
+        output_schema: dict[str, Any] | None | NotSetT = NotSet,
         serializer: Callable[[Any], str] | None = None,
         meta: dict[str, Any] | None | NotSetT = NotSet,
+        transform_args: dict[str, ArgTransform] | None = None,
         enabled: bool | None = None,
+        transform_fn: Callable[..., Any] | None = None,
     ) -> TransformedTool:
         from fastmcp.tools.tool_transform import TransformedTool
 
@@ -242,7 +242,7 @@ class FunctionTool(Tool):
         tags: set[str] | None = None,
         annotations: ToolAnnotations | None = None,
         exclude_args: list[str] | None = None,
-        output_schema: dict[str, Any] | None | NotSetT | Literal[False] = NotSet,
+        output_schema: dict[str, Any] | None | NotSetT = NotSet,
         serializer: Callable[[Any], str] | None = None,
         meta: dict[str, Any] | None = None,
         enabled: bool | None = None,
diff --git a/src/fastmcp/tools/tool_transform.py b/src/fastmcp/tools/tool_transform.py
index a51237196..7a34efa60 100644
--- a/src/fastmcp/tools/tool_transform.py
+++ b/src/fastmcp/tools/tool_transform.py
@@ -6,6 +6,7 @@ from contextvars import ContextVar
 from dataclasses import dataclass
 from typing import Annotated, Any, Literal
 
+import pydantic_core
 from mcp.types import ToolAnnotations
 from pydantic import ConfigDict
 from pydantic.fields import Field
@@ -312,11 +313,9 @@ class TransformedTool(Tool):
                         # Custom function returns ToolResult - preserve its content
                         return result
                     else:
-                        # Forwarded call with disabled schema - strip structured content
-                        return ToolResult(
-                            content=result.content,
-                            structured_content=None,
-                        )
+                        # Forwarded call with no explicit schema - preserve parent's structured content
+                        # The parent tool may have generated structured content via its own fallback logic
+                        return result
                 elif self.output_schema.get(
                     "type"
                 ) != "object" and not self.output_schema.get("x-fastmcp-wrap-result"):
@@ -334,17 +333,23 @@ class TransformedTool(Tool):
                 result, serializer=self.serializer
             )
 
-            # Handle structured content based on output schema
+            structured_output = None
+            # First handle structured content based on output schema, if any
             if self.output_schema is not None:
                 if self.output_schema.get("x-fastmcp-wrap-result"):
                     # Schema says wrap - always wrap in result key
                     structured_output = {"result": result}
                 else:
-                    # Object schemas - use result directly
-                    # User is responsible for returning dict-compatible data
                     structured_output = result
-            else:
-                structured_output = None
+            # If no output schema, try to serialize the result. If it is a dict, use
+            # it as structured content. If it is not a dict, ignore it.
+            if structured_output is None:
+                try:
+                    structured_output = pydantic_core.to_jsonable_python(result)
+                    if not isinstance(structured_output, dict):
+                        structured_output = None
+                except Exception:
+                    pass
 
             return ToolResult(
                 content=unstructured_result,
@@ -363,9 +368,9 @@ class TransformedTool(Tool):
         tags: set[str] | None = None,
         transform_fn: Callable[..., Any] | None = None,
         transform_args: dict[str, ArgTransform] | None = None,
-        annotations: ToolAnnotations | None = None,
-        output_schema: dict[str, Any] | None | Literal[False] = None,
-        serializer: Callable[[Any], str] | None = None,
+        annotations: ToolAnnotations | None | NotSetT = NotSet,
+        output_schema: dict[str, Any] | None | NotSetT = NotSet,
+        serializer: Callable[[Any], str] | None | NotSetT = NotSet,
         meta: dict[str, Any] | None | NotSetT = NotSet,
         enabled: bool | None = None,
     ) -> TransformedTool:
@@ -445,6 +450,11 @@ class TransformedTool(Tool):
         """
         transform_args = transform_args or {}
 
+        if transform_fn is not None:
+            parsed_fn = ParsedFunction.from_function(transform_fn, validate=False)
+        else:
+            parsed_fn = None
+
         # Validate transform_args
         parent_params = set(tool.parameters.get("properties", {}).keys())
         unknown_args = set(transform_args.keys()) - parent_params
@@ -457,16 +467,11 @@ class TransformedTool(Tool):
         # Always create the forwarding transform
         schema, forwarding_fn = cls._create_forwarding_transform(tool, transform_args)
 
-        # Handle output schema with smart fallback
-        if output_schema is False:
-            final_output_schema = None
-        elif output_schema is not None:
-            # Explicit schema provided - use as-is
-            final_output_schema = output_schema
-        else:
-            # Smart fallback: try custom function, then parent, then None
+        # Handle output schema
+        if output_schema is NotSet:
+            # Use smart fallback: try custom function, then parent
             if transform_fn is not None:
-                parsed_fn = ParsedFunction.from_function(transform_fn, validate=False)
+                assert parsed_fn is not None
                 final_output_schema = parsed_fn.output_schema
                 if final_output_schema is None:
                     # Check if function returns ToolResult - if so, don't fall back to parent
@@ -479,15 +484,17 @@ class TransformedTool(Tool):
                         final_output_schema = tool.output_schema
             else:
                 final_output_schema = tool.output_schema
+        else:
+            assert isinstance(output_schema, dict | None)
+            final_output_schema = output_schema
 
         if transform_fn is None:
             # User wants pure transformation - use forwarding_fn as the main function
             final_fn = forwarding_fn
             final_schema = schema
         else:
+            assert parsed_fn is not None
             # User provided custom function - merge schemas
-            if "parsed_fn" not in locals():
-                parsed_fn = ParsedFunction.from_function(transform_fn, validate=False)
             final_fn = transform_fn
 
             has_kwargs = cls._function_has_kwargs(transform_fn)
@@ -552,6 +559,13 @@ class TransformedTool(Tool):
         )
         final_title = title if not isinstance(title, NotSetT) else tool.title
         final_meta = meta if not isinstance(meta, NotSetT) else tool.meta
+        final_annotations = (
+            annotations if not isinstance(annotations, NotSetT) else tool.annotations
+        )
+        final_serializer = (
+            serializer if not isinstance(serializer, NotSetT) else tool.serializer
+        )
+        final_enabled = enabled if enabled is not None else tool.enabled
 
         transformed_tool = cls(
             fn=final_fn,
@@ -563,11 +577,11 @@ class TransformedTool(Tool):
             parameters=final_schema,
             output_schema=final_output_schema,
             tags=tags or tool.tags,
-            annotations=annotations or tool.annotations,
-            serializer=serializer or tool.serializer,
+            annotations=final_annotations,
+            serializer=final_serializer,
             meta=final_meta,
             transform_args=transform_args,
-            enabled=enabled if enabled is not None else True,
+            enabled=final_enabled,
         )
 
         return transformed_tool
diff --git a/tests/server/test_tool_transformation.py b/tests/server/test_tool_transformation.py
index 7c2095482..977d4abab 100644
--- a/tests/server/test_tool_transformation.py
+++ b/tests/server/test_tool_transformation.py
@@ -38,3 +38,31 @@ async def test_transformed_tool_filtering():
 
     tools = list(await mcp._list_tools())
     assert len(tools) == 1
+
+
+async def test_transformed_tool_structured_output_without_annotation():
+    """Test that transformed tools generate structured output when original tool has no return annotation.
+
+    Ref: https://github.com/jlowin/fastmcp/issues/1369
+    """
+    from fastmcp.client import Client
+
+    mcp = FastMCP("Test Server")
+
+    @mcp.tool()
+    def tool_without_annotation(message: str):  # No return annotation
+        """A tool without return type annotation."""
+        return {"result": "processed", "input": message}
+
+    # Create a transformed tool
+    mcp.add_tool_transformation(
+        "tool_without_annotation", ToolTransformConfig(name="transformed_tool")
+    )
+
+    # Test with client to verify structured output is populated
+    async with Client(mcp) as client:
+        result = await client.call_tool("transformed_tool", {"message": "test"})
+
+        # Structured output should be populated even without return annotation
+        assert result.data is not None
+        assert result.data == {"result": "processed", "input": "test"}
diff --git a/tests/tools/test_tool.py b/tests/tools/test_tool.py
index 03ec77331..a4583a060 100644
--- a/tests/tools/test_tool.py
+++ b/tests/tools/test_tool.py
@@ -562,7 +562,7 @@ class TestToolFromFunctionOutputSchema:
         def func() -> dict[str, str]:
             return {"message": "Hello, world!"}
 
-        tool = Tool.from_function(func, output_schema=False)
+        tool = Tool.from_function(func, output_schema=None)
         assert tool.output_schema is None
 
         result = await tool.run({})
@@ -729,17 +729,23 @@ class TestToolFromFunctionOutputSchema:
         tool_none = Tool.from_function(func, output_schema=None)
         assert tool_none.output_schema is None
 
-        # False should also disable
-        tool_false = Tool.from_function(func, output_schema=False)
-        assert tool_false.output_schema is None
+        # Default (NotSet) should infer from return type
+        tool_default = Tool.from_function(func)
+        assert (
+            tool_default.output_schema is not None
+        )  # Should infer schema from dict return type
 
-        # Both should have same behavior
+        # Different behavior: None vs inferred
         result_none = await tool_none.run({})
-        result_false = await tool_false.run({})
+        result_default = await tool_default.run({})
 
-        assert result_none.structured_content is None
-        assert result_false.structured_content is None
-        assert result_none.content[0].text == result_false.content[0].text == "123"  # type: ignore[attr-defined]
+        # None should still try fallback generation but fail for non-dict
+        assert result_none.structured_content is None  # Fallback fails for int
+        # Default should use proper schema and wrap the result
+        assert result_default.structured_content == {
+            "result": 123
+        }  # Schema-based generation with wrapping
+        assert result_none.content[0].text == result_default.content[0].text == "123"  # type: ignore[attr-defined]
 
     async def test_non_object_output_schema_raises_error(self):
         """Test that providing a non-object output schema raises a ValueError."""
@@ -1117,7 +1123,7 @@ class TestAutomaticStructuredContent:
             return UserProfile(name="Bob", age=25, email="bob@example.com")
 
         # No explicit output schema, but dataclass should still create structured content
-        tool = Tool.from_function(get_profile, output_schema=False)
+        tool = Tool.from_function(get_profile, output_schema=None)
 
         result = await tool.run({"user_id": "456"})
 
@@ -1144,8 +1150,8 @@ class TestAutomaticStructuredContent:
         def get_user_stats(user_id: str) -> UserData:
             return UserData(username="charlie", score=100, verified=True)
 
-        # Explicitly disable output schema to test automatic structured content
-        tool = Tool.from_function(get_user_stats, output_schema=False)
+        # Explicitly set output schema to None to test automatic structured content
+        tool = Tool.from_function(get_user_stats, output_schema=None)
 
         result = await tool.run({"user_id": "789"})
 
diff --git a/tests/tools/test_tool_transform.py b/tests/tools/test_tool_transform.py
index 6481791cc..f0b21bded 100644
--- a/tests/tools/test_tool_transform.py
+++ b/tests/tools/test_tool_transform.py
@@ -1020,7 +1020,12 @@ class TestEnableDisable:
         new_add = Tool.from_tool(add, name="new_add")
         mcp.add_tool(new_add)
 
-        assert new_add.enabled
+        # the new tool inherits the disabled state from the parent tool
+        assert new_add.enabled is False
+
+        new_add.enable()
+        assert new_add.enabled is True
+        assert add.enabled is False
 
         async with Client(mcp) as client:
             tools = await client.list_tools()
@@ -1118,15 +1123,15 @@ class TestTransformToolOutputSchema:
         assert new_tool.output_schema == expected_schema
         assert new_tool.output_schema == base_string_tool.output_schema
 
-    def test_transform_with_explicit_output_schema_false(self, base_string_tool):
-        """Test that output_schema=False disables structured output."""
-        new_tool = Tool.from_tool(base_string_tool, output_schema=False)
+    def test_transform_with_explicit_output_schema_none(self, base_string_tool):
+        """Test that output_schema=None sets output schema to None."""
+        new_tool = Tool.from_tool(base_string_tool, output_schema=None)
 
         assert new_tool.output_schema is None
 
-    async def test_transform_output_schema_false_runtime(self, base_string_tool):
-        """Test runtime behavior with output_schema=False."""
-        new_tool = Tool.from_tool(base_string_tool, output_schema=False)
+    async def test_transform_output_schema_none_runtime(self, base_string_tool):
+        """Test runtime behavior with output_schema=None."""
+        new_tool = Tool.from_tool(base_string_tool, output_schema=None)
 
         # Debug: check that output_schema is actually None
         assert new_tool.output_schema is None, (
@@ -1134,7 +1139,8 @@ class TestTransformToolOutputSchema:
         )
 
         result = await new_tool.run({"x": 5})
-        assert result.structured_content is None
+        # Even with output_schema=None, structured content should be generated via fallback logic
+        assert result.structured_content == {"result": "Result: 5"}
         assert result.content[0].text == "Result: 5"  # type: ignore[attr-defined]
 
     def test_transform_with_explicit_output_schema_dict(self, base_string_tool):
@@ -1306,25 +1312,27 @@ class TestTransformToolOutputSchema:
         expected_schema = TypeAdapter(dict[str, str]).json_schema()
         assert new_tool.output_schema == expected_schema
 
-    async def test_transform_output_schema_none_vs_false(self, base_string_tool):
-        """Test None vs False behavior for output_schema in transforms."""
-        # None (default) should use smart fallback (inherit from parent)
-        tool_none = Tool.from_tool(base_string_tool)  # default output_schema=None
-        assert tool_none.output_schema == base_string_tool.output_schema  # Inherits
+    async def test_transform_output_schema_default_vs_none(self, base_string_tool):
+        """Test default (NotSet) vs explicit None behavior for output_schema in transforms."""
+        # Default (NotSet) should use smart fallback (inherit from parent)
+        tool_default = Tool.from_tool(base_string_tool)  # default output_schema=NotSet
+        assert tool_default.output_schema == base_string_tool.output_schema  # Inherits
 
-        # False should explicitly disable
-        tool_false = Tool.from_tool(base_string_tool, output_schema=False)
-        assert tool_false.output_schema is None
+        # None should explicitly set output_schema to None but still generate structured content via fallback
+        tool_explicit_none = Tool.from_tool(base_string_tool, output_schema=None)
+        assert tool_explicit_none.output_schema is None
 
-        # Different behavior at runtime
-        result_none = await tool_none.run({"x": 5})
-        result_false = await tool_false.run({"x": 5})
+        # Both should generate structured content now (via different paths)
+        result_default = await tool_default.run({"x": 5})
+        result_explicit_none = await tool_explicit_none.run({"x": 5})
 
-        assert result_none.structured_content == {
+        assert result_default.structured_content == {
             "result": "Result: 5"
         }  # Inherits wrapping
-        assert result_false.structured_content is None  # Disabled
-        assert result_none.content[0].text == result_false.content[0].text  # type: ignore[attr-defined]
+        assert result_explicit_none.structured_content == {
+            "result": "Result: 5"
+        }  # Generated via fallback logic
+        assert result_default.content[0].text == result_explicit_none.content[0].text  # type: ignore[attr-defined]
 
     async def test_transform_output_schema_with_tool_result_return(
         self, base_string_tool