diff --git a/HISTORY.md b/HISTORY.md
index a6c70b79..9036e451 100644
--- a/HISTORY.md
+++ b/HISTORY.md
@@ -19,6 +19,7 @@ Our backwards-compatibility policy can be found [here](https://github.com/python
   ([#486](https://github.com/python-attrs/cattrs/pull/486))
 - **Minor change**: {py:func}`cattrs.gen.make_dict_structure_fn` will use the value for the `prefer_attrib_converters` parameter from the given converter by default now.
   If you're using this function directly, the old behavior can be restored by passing in the desired values explicitly.
+  ([#527](https://github.com/python-attrs/cattrs/issues/527) [#528](https://github.com/python-attrs/cattrs/pull/528))
 - Introduce {meth}`BaseConverter.get_structure_hook` and {meth}`BaseConverter.get_unstructure_hook` methods.
   ([#432](https://github.com/python-attrs/cattrs/issues/432) [#472](https://github.com/python-attrs/cattrs/pull/472))
 - {meth}`BaseConverter.register_structure_hook`, {meth}`BaseConverter.register_unstructure_hook`,
@@ -53,6 +54,8 @@ can now be used as decorators and have gained new features.
   ([#460](https://github.com/python-attrs/cattrs/issues/460) [#467](https://github.com/python-attrs/cattrs/pull/467))
 - `typing_extensions.Any` is now supported and handled like `typing.Any`.
   ([#488](https://github.com/python-attrs/cattrs/issues/488) [#490](https://github.com/python-attrs/cattrs/pull/490))
+- `Optional` types can now be consistently customized using `register_structure_hook` and `register_unstructure_hook`.
+  ([#529](https://github.com/python-attrs/cattrs/issues/529) [#530](https://github.com/python-attrs/cattrs/pull/530))
 - The BaseConverter now properly generates detailed validation errors for mappings.
   ([#496](https://github.com/python-attrs/cattrs/pull/496))
 - [PEP 695](https://peps.python.org/pep-0695/) generics are now tested.
diff --git a/docs/defaulthooks.md b/docs/defaulthooks.md
index c2f72b36..cee50627 100644
--- a/docs/defaulthooks.md
+++ b/docs/defaulthooks.md
@@ -36,12 +36,10 @@ Any of these hooks can be overriden if pure validation is required instead.
 ```{doctest}
 >>> c = Converter()
 
->>> def validate(value, type):
+>>> @c.register_structure_hook
+... def validate(value, type) -> int:
 ...     if not isinstance(value, type):
 ...         raise ValueError(f'{value!r} not an instance of {type}')
-...
-
->>> c.register_structure_hook(int, validate)
 
 >>> c.structure("1", int)
 Traceback (most recent call last):
@@ -110,12 +108,28 @@ Traceback (most recent call last):
 ...
 TypeError: int() argument must be a string, a bytes-like object or a number, not 'NoneType'
 
->>> cattrs.structure(None, int | None)
->>> # None was returned.
+>>> print(cattrs.structure(None, int | None))
+None
 ```
 
 Bare `Optional` s (non-parameterized, just `Optional`, as opposed to `Optional[str]`) aren't supported; `Optional[Any]` should be used instead.
 
+`Optionals` handling can be customized using {meth}`register_structure_hook` and {meth}`register_unstructure_hook`.
+
+```{doctest}
+>>> converter = Converter()
+
+>>> @converter.register_structure_hook
+... def hook(val: Any, type: Any) -> str | None:
+...     if val in ("", None):
+...         return None
+...     return str(val)
+...
+
+>>> print(converter.structure("", str | None))
+None
+```
+
 
 ### Lists
 
@@ -585,4 +599,4 @@ Protocols are unstructured according to the actual runtime type of the value.
 
 ```{versionadded} 1.9.0
 
-```
\ No newline at end of file
+```
diff --git a/docs/recipes.md b/docs/recipes.md
index 5d356e46..aeed4b92 100644
--- a/docs/recipes.md
+++ b/docs/recipes.md
@@ -10,14 +10,10 @@ In certain situations, you might want to deviate from this behavior and use alte
 
 For example, consider the following `Point` class describing points in 2D space, which offers two `classmethod`s for alternative creation:
 
-```{doctest}
->>> from __future__ import annotations
-
+```{doctest} point_group
 >>> import math
-
 >>> from attrs import define
 
-
 >>> @define
 ... class Point:
 ...     """A point in 2D space."""
@@ -25,12 +21,12 @@ For example, consider the following `Point` class describing points in 2D space,
 ...     y: float
 ...
 ...     @classmethod
-...     def from_tuple(cls, coordinates: tuple[float, float]) -> Point:
+...     def from_tuple(cls, coordinates: tuple[float, float]) -> "Point":
 ...         """Create a point from a tuple of Cartesian coordinates."""
 ...         return Point(*coordinates)
 ...
 ...     @classmethod
-...     def from_polar(cls, radius: float, angle: float) -> Point:
+...     def from_polar(cls, radius: float, angle: float) -> "Point":
 ...         """Create a point from its polar coordinates."""
 ...         return Point(radius * math.cos(angle), radius * math.sin(angle))
 ```
@@ -40,7 +36,7 @@ For example, consider the following `Point` class describing points in 2D space,
 
 A simple way to _statically_ set one of the `classmethod`s as initializer is to register a structuring hook that holds a reference to the respective callable:
 
-```{doctest}
+```{doctest} point_group
 >>> from inspect import signature
 >>> from typing import Callable, TypedDict
 
@@ -48,9 +44,10 @@ A simple way to _statically_ set one of the `classmethod`s as initializer is to
 >>> from cattrs.dispatch import StructureHook
 
 >>> def signature_to_typed_dict(fn: Callable) -> type[TypedDict]:
-...    """Create a TypedDict reflecting a callable's signature."""
+...     """Create a TypedDict reflecting a callable's signature."""
 ...     params = {p: t.annotation for p, t in signature(fn).parameters.items()}
 ...     return TypedDict(f"{fn.__name__}_args", params)
+...
 
 >>> def make_initializer_from(fn: Callable, conv: Converter) -> StructureHook:
 ...     """Return a structuring hook from a given callable."""
@@ -61,7 +58,7 @@ A simple way to _statically_ set one of the `classmethod`s as initializer is to
 
 Now, you can easily structure `Point`s from the specified alternative representation:
 
-```{doctest}
+```{doctest} point_group
 >>> c = Converter()
 >>> c.register_structure_hook(Point, make_initializer_from(Point.from_polar, c))
 
@@ -78,7 +75,7 @@ A typical scenario would be when object structuring happens behind an API and yo
 
 In such situations, the following hook factory can help you achieve your goal:
 
-```{doctest}
+```{doctest} point_group
 >>> from inspect import signature
 >>> from typing import Callable, TypedDict
 
@@ -90,6 +87,7 @@ In such situations, the following hook factory can help you achieve your goal:
 ...     params = {p: t.annotation for p, t in signature(fn).parameters.items()}
 ...     return TypedDict(f"{fn.__name__}_args", params)
 
+>>> T = TypeVar("T")
 >>> def make_initializer_selection_hook(
 ...     initializer_key: str,
 ...     converter: Converter,
@@ -116,7 +114,7 @@ In such situations, the following hook factory can help you achieve your goal:
 
 Specifying the key that determines the initializer to be used now lets you dynamically select the `classmethod` as part of the object specification itself:
 
-```{doctest}
+```{doctest} point_group
 >>> c = Converter()
 >>> c.register_structure_hook(Point, make_initializer_selection_hook("initializer", c))
 
diff --git a/src/cattrs/converters.py b/src/cattrs/converters.py
index 4bed9991..5ca1d065 100644
--- a/src/cattrs/converters.py
+++ b/src/cattrs/converters.py
@@ -23,6 +23,7 @@
     OriginMutableSet,
     Sequence,
     Set,
+    TypeAlias,
     fields,
     get_final_base,
     get_newtype_base,
@@ -245,12 +246,12 @@ def __init__(
                 (is_namedtuple, namedtuple_structure_factory, "extended"),
                 (is_mapping, self._structure_dict),
                 (is_supported_union, self._gen_attrs_union_structure, True),
+                (is_optional, self._structure_optional),
                 (
                     lambda t: is_union_type(t) and t in self._union_struct_registry,
                     self._union_struct_registry.__getitem__,
                     True,
                 ),
-                (is_optional, self._structure_optional),
                 (has, self._structure_attrs),
             ]
         )
@@ -1382,4 +1383,4 @@ def copy(
         return res
 
 
-GenConverter = Converter
+GenConverter: TypeAlias = Converter
diff --git a/tests/test_optionals.py b/tests/test_optionals.py
index 5eec5c0b..2fca1de6 100644
--- a/tests/test_optionals.py
+++ b/tests/test_optionals.py
@@ -3,7 +3,7 @@
 import pytest
 from attrs import define
 
-from cattrs import Converter
+from cattrs import BaseConverter, Converter
 
 from ._compat import is_py310_plus
 
@@ -51,3 +51,23 @@ class A:
         pass
 
     assert converter.unstructure(A(), Optional[Any]) == {}
+
+
+def test_override_optional(converter: BaseConverter):
+    """Optionals can be overridden using singledispatch."""
+
+    @converter.register_structure_hook
+    def _(val, _) -> Optional[int]:
+        if val in ("", None):
+            return None
+        return int(val)
+
+    assert converter.structure("", Optional[int]) is None
+
+    @converter.register_unstructure_hook
+    def _(val: Optional[int]) -> Any:
+        if val in (None, 0):
+            return None
+        return val
+
+    assert converter.unstructure(0, Optional[int]) is None