diff --git a/HISTORY.md b/HISTORY.md
index e1b5298d..7a215d32 100644
--- a/HISTORY.md
+++ b/HISTORY.md
@@ -19,6 +19,8 @@ Our backwards-compatibility policy can be found [here](https://github.com/python
   ([#698](https://github.com/python-attrs/cattrs/pull/698))
 - Apply the attrs converter to the default value before checking if it is equal to the attribute's value, when `omit_if_default` is true and an attrs converter is specified.
   ([#696](https://github.com/python-attrs/cattrs/pull/696))
+- Unstructure enum values and structure enum values if they have a type hinted `_value_` attribute.
+  ([##699](https://github.com/python-attrs/cattrs/issues/699))
 
 ## 25.3.0 (2025-10-07)
 
diff --git a/docs/defaulthooks.md b/docs/defaulthooks.md
index de75c857..1b68ca21 100644
--- a/docs/defaulthooks.md
+++ b/docs/defaulthooks.md
@@ -53,7 +53,6 @@ When unstructuring, these types are passed through unchanged.
 ### Enums
 
 Enums are structured by their values, and unstructured to their values.
-This works even for complex values, like tuples.
 
 ```{doctest}
 
@@ -70,6 +69,30 @@ This works even for complex values, like tuples.
 'siamese'
 ```
 
+Enum structuring and unstructuring even works for complex values, like tuples, but if you have anything but simple literal types in those tuples (`str`, `bool`, `int`, `float`) you should consider defining the Enum value's type via the `_value_` attribute's type hint so that cattrs can properly structure it.
+
+```{doctest}
+
+>>> @unique
+... class VideoStandard(Enum):
+...    NTSC = "ntsc"
+...    PAL = "pal"
+
+>>> @unique
+... class Resolution(Enum):
+...     _value_: tuple[VideoStandard, int]
+...     NTSC_0 = (VideoStandard.NTSC, 0)
+...     PAL_0 = (VideoStandard.PAL, 0)
+...     NTSC_1 = (VideoStandard.NTSC, 1)
+...     PAL_1 = (VideoStandard.PAL, 1)
+
+>>> cattrs.structure(("ntsc", 1), Resolution)
+<Resolution.NTSC_1: (<VideoStandard.NTSC: 'ntsc'>, 1)>
+
+>>> cattrs.unstructure(Resolution.PAL_0)
+['pal', 0]
+```
+
 Again, in case of errors, the expected exceptions are raised.
 
 ### `pathlib.Path`
diff --git a/src/cattrs/converters.py b/src/cattrs/converters.py
index 13f63ee1..c4dc33f8 100644
--- a/src/cattrs/converters.py
+++ b/src/cattrs/converters.py
@@ -9,7 +9,7 @@
 from inspect import Signature
 from inspect import signature as inspect_signature
 from pathlib import Path
-from typing import Any, Optional, Tuple, TypeVar, overload
+from typing import Any, Optional, Tuple, TypeVar, get_type_hints, overload
 
 from attrs import Attribute, resolve_types
 from attrs import has as attrs_has
@@ -308,7 +308,7 @@ def __init__(
                 (bytes, self._structure_call),
                 (int, self._structure_call),
                 (float, self._structure_call),
-                (Enum, self._structure_call),
+                (Enum, self._structure_enum),
                 (Path, self._structure_call),
             ]
         )
@@ -631,8 +631,8 @@ def unstructure_attrs_astuple(self, obj: Any) -> tuple[Any, ...]:
         return tuple(res)
 
     def _unstructure_enum(self, obj: Enum) -> Any:
-        """Convert an enum to its value."""
-        return obj.value
+        """Convert an enum to its unstructured value."""
+        return self._unstructure_func.dispatch(obj.value.__class__)(obj.value)
 
     def _unstructure_seq(self, seq: Sequence[T]) -> Sequence[T]:
         """Convert a sequence to primitive equivalents."""
@@ -713,6 +713,16 @@ def _structure_simple_literal(val, type):
             raise Exception(f"{val} not in literal {type}")
         return val
 
+    def _structure_enum(self, val: Any, cl: type[Enum]) -> Enum:
+        """Structure ``val`` if possible and return the enum it corresponds to.
+
+        Uses type hints for the "_value_" attribute if they exist to structure
+        the enum values before returning the result."""
+        hints = get_type_hints(cl)
+        if "_value_" in hints:
+            val = self.structure(val, hints["_value_"])
+        return cl(val)
+
     @staticmethod
     def _structure_enum_literal(val, type):
         vals = {(x.value if isinstance(x, Enum) else x): x for x in type.__args__}
diff --git a/tests/test_enums.py b/tests/test_enums.py
index 59ebb6b6..c17760fd 100644
--- a/tests/test_enums.py
+++ b/tests/test_enums.py
@@ -1,5 +1,7 @@
 """Tests for enums."""
 
+from enum import Enum
+
 from hypothesis import given
 from hypothesis.strategies import data, sampled_from
 from pytest import raises
@@ -29,3 +31,31 @@ def test_enum_failure(enum):
         converter.structure("", type)
 
     assert exc_info.value.args[0] == f" not in literal {type!r}"
+
+
+class SimpleEnum(Enum):
+    _value_: int
+    A = 0
+    B = 1
+    C = 2
+
+
+class ComplexEnum(Enum):
+    _value_: tuple[SimpleEnum, int]
+    A0 = (SimpleEnum.A, 0)
+    A1 = (SimpleEnum.A, 1)
+    B1 = (SimpleEnum.B, 1)
+    B2 = (SimpleEnum.B, 2)
+    C1 = (SimpleEnum.C, 1)
+
+
+def test_unstructure_complex_enum() -> None:
+    converter = BaseConverter()
+    assert converter.unstructure(SimpleEnum.A) == 0
+    assert converter.unstructure(ComplexEnum.A1) == (0, 1)
+
+
+def test_structure_complex_enum() -> None:
+    converter = BaseConverter()
+    assert converter.structure(0, SimpleEnum) == SimpleEnum.A
+    assert converter.structure((0, 1), ComplexEnum) == ComplexEnum.A1