diff --git a/src/fastmcp/tools/base.py b/src/fastmcp/tools/base.py
index b704016fa..223413aaa 100644
--- a/src/fastmcp/tools/base.py
+++ b/src/fastmcp/tools/base.py
@@ -290,6 +290,10 @@ class Tool(FastMCPComponent):
 
         content = _convert_to_content(raw_value, serializer=self.serializer)
 
+        # Bytes can't be represented as structured JSON content
+        if isinstance(raw_value, bytes):
+            return ToolResult(content=content)
+
         # Skip structured content for ContentBlock types only if no output_schema
         # (if output_schema exists, MCP SDK requires structured_content)
         if self.output_schema is None and (
@@ -303,7 +307,7 @@ class Tool(FastMCPComponent):
 
         try:
             structured = pydantic_core.to_jsonable_python(raw_value)
-        except pydantic_core.PydanticSerializationError:
+        except (pydantic_core.PydanticSerializationError, UnicodeDecodeError):
             return ToolResult(content=content)
 
         if self.output_schema is None:
@@ -492,6 +496,14 @@ def _convert_to_single_content_block(
     if isinstance(item, str):
         return TextContent(type="text", text=item)
 
+    if isinstance(item, bytes):
+        try:
+            return TextContent(type="text", text=item.decode("utf-8"))
+        except UnicodeDecodeError:
+            import base64
+
+            return TextContent(type="text", text=base64.b64encode(item).decode("ascii"))
+
     return TextContent(type="text", text=_serialize_with_fallback(item, serializer))
 
 
diff --git a/src/fastmcp/tools/function_parsing.py b/src/fastmcp/tools/function_parsing.py
index 804dc6efd..21d10cb79 100644
--- a/src/fastmcp/tools/function_parsing.py
+++ b/src/fastmcp/tools/function_parsing.py
@@ -39,6 +39,16 @@ except ImportError:
     _PREFAB_TYPES = ()
 
 
+def _contains_bytes_type(tp: Any) -> bool:
+    """Check if *tp* is or contains bytes, recursing through unions and Annotated."""
+    if tp is bytes:
+        return True
+    origin = get_origin(tp)
+    if origin is Union or origin is types.UnionType or origin is Annotated:
+        return any(_contains_bytes_type(a) for a in get_args(tp))
+    return False
+
+
 def _contains_prefab_type(tp: Any) -> bool:
     """Check if *tp* is or contains a prefab type, recursing through unions and Annotated."""
     if isinstance(tp, type) and issubclass(tp, _PREFAB_TYPES):
@@ -205,6 +215,10 @@ class ParsedFunction:
         original_output_type = output_type
 
         if output_type not in (inspect._empty, None, Any, ...):
+            # bytes can't be represented as structured JSON output — skip schema
+            if _contains_bytes_type(output_type):
+                output_type = _UnserializableType
+
             # Prefab component subclasses (Column, Card, etc.) shouldn't
             # produce output schemas — replace_type only does exact matching,
             # so we handle subclass matching explicitly here.  We also need
diff --git a/src/fastmcp/tools/function_tool.py b/src/fastmcp/tools/function_tool.py
index 8dfc47f60..cb79b72cc 100644
--- a/src/fastmcp/tools/function_tool.py
+++ b/src/fastmcp/tools/function_tool.py
@@ -255,6 +255,9 @@ class FunctionTool(Tool):
                         # Handle sync wrappers that return awaitables
                         if inspect.isawaitable(result):
                             result = await result
+                    # Materialize generators inside timeout scope so slow
+                    # generators don't run past the configured timeout
+                    result = await self._materialize_generator(result)
             except TimeoutError:
                 logger.warning(
                     f"Tool '{self.name}' timed out after {self.timeout}s. "
@@ -277,9 +280,24 @@ class FunctionTool(Tool):
                 )
                 if inspect.isawaitable(result):
                     result = await result
+            result = await self._materialize_generator(result)
 
         return self.convert_result(result)
 
+    @staticmethod
+    async def _materialize_generator(result: Any) -> Any:
+        """Consume generators/async generators into lists.
+
+        Without this, async generators pass through as objects (repr string),
+        and sync generators get consumed during text serialization but are
+        exhausted by the time structured content is built.
+        """
+        if inspect.isasyncgen(result):
+            return [item async for item in result]
+        if inspect.isgenerator(result):
+            return list(result)
+        return result
+
     def register_with_docket(self, docket: Docket) -> None:
         """Register this tool with docket for background execution.
 
diff --git a/tests/server/providers/local_provider_tools/test_local_provider_tools.py b/tests/server/providers/local_provider_tools/test_local_provider_tools.py
index 9e1803b41..292365bc4 100644
--- a/tests/server/providers/local_provider_tools/test_local_provider_tools.py
+++ b/tests/server/providers/local_provider_tools/test_local_provider_tools.py
@@ -67,7 +67,9 @@ class TestToolReturnTypes:
             return b"Hello, world!"
 
         result = await mcp.call_tool("bytes_tool", {})
-        assert result.structured_content == {"result": "Hello, world!"}
+        # bytes can't be represented as structured JSON, so no structured_content
+        assert result.structured_content is None
+        assert result.content[0].text == "Hello, world!"  # ty:ignore[unresolved-attribute]
 
     async def test_uuid(self):
         mcp = FastMCP()
diff --git a/tests/server/tasks/test_task_return_types.py b/tests/server/tasks/test_task_return_types.py
index 3ef352902..f29f1e19b 100644
--- a/tests/server/tasks/test_task_return_types.py
+++ b/tests/server/tasks/test_task_return_types.py
@@ -258,8 +258,9 @@ async def binary_type_server():
     [
         (
             "return_bytes",
-            str,
-            lambda r: "Hello bytes!" in r.data or "SGVsbG8gYnl0ZXMh" in r.data,
+            type(None),
+            lambda r: r.data is None
+            and any("Hello bytes!" in c.text for c in r.content),
         ),
         (
             "return_uuid",