diff --git a/HISTORY.md b/HISTORY.md
index 942616e3..c34b9d9d 100644
--- a/HISTORY.md
+++ b/HISTORY.md
@@ -13,6 +13,8 @@ Our backwards-compatibility policy can be found [here](https://github.com/python
 
 ## NEXT
 
+- The tagged union strategy ({func}`cattrs.strategies.configure_tagged_union`) now also handles the configured union extended with `None` (for example a field typed `Union[A, B] | None`), keeping the tag for members and passing `None` through.
+  ([#345](https://github.com/python-attrs/cattrs/issues/345))
 - Fix the msgspec converter passing typed deques directly to the encoder, which cannot serialize them. Deques are now unstructured into lists, including when nested in attrs classes or dataclasses.
   ([#818](https://github.com/python-attrs/cattrs/issues/818) [#819](https://github.com/python-attrs/cattrs/pull/819))
 
diff --git a/src/cattrs/strategies/_unions.py b/src/cattrs/strategies/_unions.py
index 52ac6a95..40c9c87d 100644
--- a/src/cattrs/strategies/_unions.py
+++ b/src/cattrs/strategies/_unions.py
@@ -1,4 +1,5 @@
 from collections import defaultdict
+from types import NoneType
 from typing import Any, Callable, Union
 
 from attrs import NOTHING, NothingType
@@ -49,6 +50,10 @@ def configure_tagged_union(
 
     ..  versionchanged:: 25.1
         Type aliases of unions are now also supported.
+    ..  versionchanged:: NEXT
+        The union extended with `None` (for example a field typed
+        `Union[A, B] | None`) is now handled too, with `None` passing
+        through.
     """
     if is_type_alias(union):
         union = union.__value__
@@ -125,6 +130,33 @@ def unstructure_tagged_union(
     converter.register_unstructure_hook(union, unstructure_tagged_union)
     converter.register_structure_hook(union, structure_tagged_union)
 
+    if NoneType not in args:
+        # Also handle the union extended with `None`, so fields typed
+        # `Optional[Union[...]]` (or `Union[...] | None`) keep the tag and
+        # can be disambiguated, with `None` passing through untouched.
+        optional_union = Union[(*args, NoneType)]
+
+        def structure_optional_tagged_union(
+            val: dict | None, _, _h=structure_tagged_union
+        ) -> union:
+            if val is None:
+                return None
+            return _h(val, _)
+
+        def unstructure_optional_tagged_union(
+            val: union | None, _h=unstructure_tagged_union
+        ) -> dict | None:
+            if val is None:
+                return None
+            return _h(val)
+
+        converter.register_unstructure_hook(
+            optional_union, unstructure_optional_tagged_union
+        )
+        converter.register_structure_hook(
+            optional_union, structure_optional_tagged_union
+        )
+
     for cl in args:
         tag = tag_generator(cl)
         struct_handler = converter.get_structure_hook(cl)
diff --git a/tests/strategies/test_tagged_unions.py b/tests/strategies/test_tagged_unions.py
index ba5ae49b..e1170c1e 100644
--- a/tests/strategies/test_tagged_unions.py
+++ b/tests/strategies/test_tagged_unions.py
@@ -177,3 +177,48 @@ class Top:
 
     data = c.unstructure(Top(u=[B(a="")]), Top)
     c.structure(data, Top)
+
+
+def test_optional_union(converter: BaseConverter) -> None:
+    """The union extended with `None` is handled too.
+
+    Regression test for https://github.com/python-attrs/cattrs/issues/345
+    """
+    union = Union[A, B]
+    configure_tagged_union(union, converter)
+
+    optional = Optional[union]
+
+    assert converter.unstructure(A(1), optional) == {"_type": "A", "a": 1}
+    assert converter.unstructure(B("1"), optional) == {"_type": "B", "a": "1"}
+    assert converter.unstructure(None, optional) is None
+
+    assert converter.structure({"_type": "A", "a": 1}, optional) == A(1)
+    assert converter.structure({"_type": "B", "a": 1}, optional) == B("1")
+    assert converter.structure(None, optional) is None
+
+
+def test_optional_union_in_class(converter: BaseConverter) -> None:
+    """Optional tagged unions work as class fields, in both spellings."""
+    union = Union[A, B]
+    configure_tagged_union(union, converter)
+
+    @define
+    class Holder:
+        c: Union[A, B, None]
+
+    @define
+    class TypingHolder:
+        c: Optional[Union[A, B]]
+
+    assert converter.unstructure(Holder(B("1"))) == {"c": {"_type": "B", "a": "1"}}
+    assert converter.unstructure(Holder(None)) == {"c": None}
+    assert converter.structure({"c": {"_type": "B", "a": "1"}}, Holder) == Holder(
+        B("1")
+    )
+    assert converter.structure({"c": None}, Holder) == Holder(None)
+
+    assert converter.unstructure(TypingHolder(B("1"))) == {
+        "c": {"_type": "B", "a": "1"}
+    }
+    assert converter.structure({"c": None}, TypingHolder) == TypingHolder(None)