diff --git a/tests/test_annotated.py b/tests/test_annotated.py
index 25622d0ebf..09072b3ae1 100644
--- a/tests/test_annotated.py
+++ b/tests/test_annotated.py
@@ -1,6 +1,3 @@
-from enum import Enum
-from typing import Union
-
 import typer
 from typer.testing import CliRunner
 from typing_extensions import Annotated
@@ -79,66 +76,3 @@ def cmd(force: Annotated[bool, typer.Option("--force")] = False):
     result = runner.invoke(app, ["--force"])
     assert result.exit_code == 0, result.output
     assert "Forcing operation" in result.output
-
-
-class TestAnnotatedOptionAcceptsOptionalValue:
-    def test_enum(self):
-        app = typer.Typer()
-
-        class OptEnum(str, Enum):
-            val1 = "val1"
-            val2 = "val2"
-
-        @app.command()
-        def cmd(opt: Annotated[Union[bool, OptEnum], typer.Option()] = OptEnum.val1):
-            if opt is False:
-                print("False")
-            elif opt is True:
-                print("True")
-            else:
-                print(opt.value)
-
-        result = runner.invoke(app)
-        assert result.exit_code == 0, result.output
-        assert "False" in result.output
-
-        result = runner.invoke(app, ["--opt"])
-        assert result.exit_code == 0, result.output
-        assert "val1" in result.output
-
-        result = runner.invoke(app, ["--opt", "val1"])
-        assert result.exit_code == 0, result.output
-        assert "val1" in result.output
-
-        result = runner.invoke(app, ["--opt", "val2"])
-        assert result.exit_code == 0, result.output
-        assert "val2" in result.output
-
-        result = runner.invoke(app, ["--opt", "val3"])
-        assert result.exit_code != 0
-        assert "Invalid value for '--opt': 'val3' is not one of" in result.output
-
-    def test_int(self):
-        app = typer.Typer()
-
-        @app.command()
-        def cmd(opt: Annotated[Union[bool, int], typer.Option()] = 1):
-            print(opt)
-
-        result = runner.invoke(app)
-        assert result.exit_code == 0, result.output
-        assert "False" in result.output
-
-        result = runner.invoke(app, ["--opt"])
-        assert result.exit_code == 0, result.output
-        assert "1" in result.output
-
-        result = runner.invoke(app, ["--opt", "2"])
-        assert result.exit_code == 0, result.output
-        assert "2" in result.output
-
-        result = runner.invoke(app, ["--opt", "test"])
-        assert result.exit_code != 0
-        assert (
-            "Invalid value for '--opt': 'test' is not a valid integer" in result.output
-        )
diff --git a/tests/test_type_conversion.py b/tests/test_type_conversion.py
index 904a686d2e..0102ac1d2d 100644
--- a/tests/test_type_conversion.py
+++ b/tests/test_type_conversion.py
@@ -1,11 +1,12 @@
 from enum import Enum
 from pathlib import Path
-from typing import Any, List, Optional, Tuple
+from typing import Any, List, Optional, Tuple, Union
 
 import click
 import pytest
 import typer
 from typer.testing import CliRunner
+from typing_extensions import Annotated
 
 from .utils import needs_py310
 
@@ -169,3 +170,101 @@ def custom_click_type(
 
     result = runner.invoke(app, ["0x56"])
     assert result.exit_code == 0
+
+
+class TestOptionAcceptsOptionalValue:
+    def test_enum(self):
+        app = typer.Typer()
+
+        class OptEnum(str, Enum):
+            val1 = "val1"
+            val2 = "val2"
+
+        @app.command()
+        def cmd(opt: Annotated[Union[bool, OptEnum], typer.Option()] = OptEnum.val1):
+            if opt is False:
+                print("False")
+
+            else:
+                print(opt.value)
+
+        result = runner.invoke(app)
+        assert result.exit_code == 0, result.output
+        assert "False" in result.output
+
+        result = runner.invoke(app, ["--opt"])
+        assert result.exit_code == 0, result.output
+        assert "val1" in result.output
+
+        result = runner.invoke(app, ["--opt", "val1"])
+        assert result.exit_code == 0, result.output
+        assert "val1" in result.output
+
+        result = runner.invoke(app, ["--opt", "val2"])
+        assert result.exit_code == 0, result.output
+        assert "val2" in result.output
+
+        result = runner.invoke(app, ["--opt", "val3"])
+        assert result.exit_code != 0
+        assert "Invalid value for '--opt': 'val3' is not one of" in result.output
+
+        result = runner.invoke(app, ["--opt", "0"])
+        assert result.exit_code == 0, result.output
+        assert "False" in result.output
+
+        result = runner.invoke(app, ["--opt", "1"])
+        assert result.exit_code == 0, result.output
+        assert "val1" in result.output
+
+    def test_int(self):
+        app = typer.Typer()
+
+        @app.command()
+        def cmd(opt: Annotated[Union[bool, int], typer.Option()] = 1):
+            print(opt)
+
+        result = runner.invoke(app)
+        assert result.exit_code == 0, result.output
+        assert "False" in result.output
+
+        result = runner.invoke(app, ["--opt"])
+        assert result.exit_code == 0, result.output
+        assert "1" in result.output
+
+        result = runner.invoke(app, ["--opt", "2"])
+        assert result.exit_code == 0, result.output
+        assert "2" in result.output
+
+        result = runner.invoke(app, ["--opt", "test"])
+        assert result.exit_code != 0
+        assert (
+            "Invalid value for '--opt': 'test' is not a valid integer" in result.output
+        )
+
+        result = runner.invoke(app, ["--opt", "true"])
+        assert result.exit_code == 0, result.output
+        assert "1" in result.output
+
+        result = runner.invoke(app, ["--opt", "off"])
+        assert result.exit_code == 0, result.output
+        assert "False" in result.output
+
+    def test_path(self):
+        app = typer.Typer()
+
+        @app.command()
+        def cmd(opt: Annotated[Union[bool, Path], typer.Option()] = Path(".")):
+            if isinstance(opt, Path):
+                print((opt / "file.py").as_posix())
+
+        result = runner.invoke(app, ["--opt"])
+        assert result.exit_code == 0, result.output
+        assert "file.py" in result.output
+
+        result = runner.invoke(app, ["--opt", "/test/path/file.py"])
+        assert result.exit_code == 0, result.output
+        assert "/test/path/file.py" in result.output
+
+        result = runner.invoke(app, ["--opt", "False"])
+        assert result.exit_code == 0, result.output
+        assert "file.py" not in result.output
diff --git a/typer/main.py b/typer/main.py
index 53270b119e..93bb0b378f 100644
--- a/typer/main.py
+++ b/typer/main.py
@@ -660,19 +660,21 @@ def generate_enum_convertor(
 ) -> Callable[[Any], Union[None, bool, Enum]]:
     val_map = {str(val.value): val for val in enum}
 
-    def convertor(value: Any) -> Union[None, bool, Enum]:
-        if value is None:
-            return None
-
+    def convertor(value: Any) -> Union[bool, Enum]:
         if isinstance(value, bool) and skip_bool:
             return value
 
+        if isinstance(value, enum):
+            return value
+
         val = str(value)
         if val in val_map:
             key = val_map[val]
             return enum(key)
 
-        return None
+        raise click.BadParameter(
+            f"Invalid value '{value}' for enum '{enum.__name__}'"
+        )  # pragma: no cover
 
     return convertor
 
@@ -845,22 +847,6 @@ def __init__(self, type_: click.ParamType, default: Any) -> None:
         self._default: Any = default
         self.name: str = f"BOOLEAN|{type_.name}"
 
-    @override
-    def __repr__(self) -> str:
-        return f"DefaultOption({self._type})"
-
-    @override
-    def to_info_dict(self) -> Dict[str, Any]:
-        return self._type.to_info_dict()
-
-    @override
-    def get_metavar(self, param: click.Parameter) -> Optional[str]:
-        return self._type.get_metavar(param)
-
-    @override
-    def get_missing_message(self, param: click.Parameter) -> Optional[str]:
-        return self._type.get_missing_message(param)
-
     @override
     def convert(
         self, value: Any, param: Optional[click.Parameter], ctx: Optional[click.Context]
@@ -895,9 +881,6 @@ class DefaultFalse:
     def __init__(self, value: Any) -> None:
         self._value = value
 
-    def __repr__(self) -> str:
-        return f"False ({repr(self._value)})"
-
     def __str__(self) -> str:
         return f"False ({str(self._value)})"