diff --git a/mypy/checker.py b/mypy/checker.py
index b786155079e5..3bd9c494a890 100644
--- a/mypy/checker.py
+++ b/mypy/checker.py
@@ -7216,22 +7216,32 @@ def is_unsafe_overlapping_overload_signatures(
     #
     # This discrepancy is unfortunately difficult to get rid of, so we repeat the
     # checks twice in both directions for now.
+    #
+    # Note that we ignore possible overlap between type variables and None. This
+    # is technically unsafe, but unsafety is tiny and this prevents some common
+    # use cases like:
+    #     @overload
+    #     def foo(x: None) -> None: ..
+    #     @overload
+    #     def foo(x: T) -> Foo[T]: ...
     return is_callable_compatible(
         signature,
         other,
-        is_compat=is_overlapping_types_no_promote_no_uninhabited,
+        is_compat=is_overlapping_types_no_promote_no_uninhabited_no_none,
         is_compat_return=lambda l, r: not is_subtype_no_promote(l, r),
         ignore_return=False,
         check_args_covariantly=True,
         allow_partial_overlap=True,
+        no_unify_none=True,
     ) or is_callable_compatible(
         other,
         signature,
-        is_compat=is_overlapping_types_no_promote_no_uninhabited,
+        is_compat=is_overlapping_types_no_promote_no_uninhabited_no_none,
         is_compat_return=lambda l, r: not is_subtype_no_promote(r, l),
         ignore_return=False,
         check_args_covariantly=False,
         allow_partial_overlap=True,
+        no_unify_none=True,
     )
 
 
@@ -7717,12 +7727,18 @@ def is_subtype_no_promote(left: Type, right: Type) -> bool:
     return is_subtype(left, right, ignore_promotions=True)
 
 
-def is_overlapping_types_no_promote_no_uninhabited(left: Type, right: Type) -> bool:
+def is_overlapping_types_no_promote_no_uninhabited_no_none(left: Type, right: Type) -> bool:
     # For the purpose of unsafe overload checks we consider list[<nothing>] and list[int]
     # non-overlapping. This is consistent with how we treat list[int] and list[str] as
     # non-overlapping, despite [] belongs to both. Also this will prevent false positives
     # for failed type inference during unification.
-    return is_overlapping_types(left, right, ignore_promotions=True, ignore_uninhabited=True)
+    return is_overlapping_types(
+        left,
+        right,
+        ignore_promotions=True,
+        ignore_uninhabited=True,
+        prohibit_none_typevar_overlap=True,
+    )
 
 
 def is_private(node_name: str) -> bool:
diff --git a/mypy/checkexpr.py b/mypy/checkexpr.py
index 9e46d9ee39cb..3282ee338b87 100644
--- a/mypy/checkexpr.py
+++ b/mypy/checkexpr.py
@@ -2400,6 +2400,11 @@ def check_overload_call(
         #         typevar. See https://github.com/python/mypy/issues/4063 for related discussion.
         erased_targets: list[CallableType] | None = None
         unioned_result: tuple[Type, Type] | None = None
+
+        # Determine whether we need to encourage union math. This should be generally safe,
+        # as union math infers better results in the vast majority of cases, but it is very
+        # computationally intensive.
+        none_type_var_overlap = self.possible_none_type_var_overlap(arg_types, plausible_targets)
         union_interrupted = False  # did we try all union combinations?
         if any(self.real_union(arg) for arg in arg_types):
             try:
@@ -2412,6 +2417,7 @@ def check_overload_call(
                         arg_names,
                         callable_name,
                         object_type,
+                        none_type_var_overlap,
                         context,
                     )
             except TooManyUnions:
@@ -2444,8 +2450,10 @@ def check_overload_call(
         # If any of checks succeed, stop early.
         if inferred_result is not None and unioned_result is not None:
             # Both unioned and direct checks succeeded, choose the more precise type.
-            if is_subtype(inferred_result[0], unioned_result[0]) and not isinstance(
-                get_proper_type(inferred_result[0]), AnyType
+            if (
+                is_subtype(inferred_result[0], unioned_result[0])
+                and not isinstance(get_proper_type(inferred_result[0]), AnyType)
+                and not none_type_var_overlap
             ):
                 return inferred_result
             return unioned_result
@@ -2495,7 +2503,8 @@ def check_overload_call(
             callable_name=callable_name,
             object_type=object_type,
         )
-        if union_interrupted:
+        # Do not show the extra error if the union math was forced.
+        if union_interrupted and not none_type_var_overlap:
             self.chk.fail(message_registry.TOO_MANY_UNION_COMBINATIONS, context)
         return result
 
@@ -2650,6 +2659,44 @@ def overload_erased_call_targets(
                 matches.append(typ)
         return matches
 
+    def possible_none_type_var_overlap(
+        self, arg_types: list[Type], plausible_targets: list[CallableType]
+    ) -> bool:
+        """Heuristic to determine whether we need to try forcing union math.
+
+        This is needed to avoid greedy type variable match in situations like this:
+            @overload
+            def foo(x: None) -> None: ...
+            @overload
+            def foo(x: T) -> list[T]: ...
+
+            x: int | None
+            foo(x)
+        we want this call to infer list[int] | None, not list[int | None].
+        """
+        if not plausible_targets or not arg_types:
+            return False
+        has_optional_arg = False
+        for arg_type in get_proper_types(arg_types):
+            if not isinstance(arg_type, UnionType):
+                continue
+            for item in get_proper_types(arg_type.items):
+                if isinstance(item, NoneType):
+                    has_optional_arg = True
+                    break
+        if not has_optional_arg:
+            return False
+
+        min_prefix = min(len(c.arg_types) for c in plausible_targets)
+        for i in range(min_prefix):
+            if any(
+                isinstance(get_proper_type(c.arg_types[i]), NoneType) for c in plausible_targets
+            ) and any(
+                isinstance(get_proper_type(c.arg_types[i]), TypeVarType) for c in plausible_targets
+            ):
+                return True
+        return False
+
     def union_overload_result(
         self,
         plausible_targets: list[CallableType],
@@ -2659,6 +2706,7 @@ def union_overload_result(
         arg_names: Sequence[str | None] | None,
         callable_name: str | None,
         object_type: Type | None,
+        none_type_var_overlap: bool,
         context: Context,
         level: int = 0,
     ) -> list[tuple[Type, Type]] | None:
@@ -2698,20 +2746,23 @@ def union_overload_result(
 
         # Step 3: Try a direct match before splitting to avoid unnecessary union splits
         # and save performance.
-        with self.type_overrides_set(args, arg_types):
-            direct = self.infer_overload_return_type(
-                plausible_targets,
-                args,
-                arg_types,
-                arg_kinds,
-                arg_names,
-                callable_name,
-                object_type,
-                context,
-            )
-        if direct is not None and not isinstance(get_proper_type(direct[0]), (UnionType, AnyType)):
-            # We only return non-unions soon, to avoid greedy match.
-            return [direct]
+        if not none_type_var_overlap:
+            with self.type_overrides_set(args, arg_types):
+                direct = self.infer_overload_return_type(
+                    plausible_targets,
+                    args,
+                    arg_types,
+                    arg_kinds,
+                    arg_names,
+                    callable_name,
+                    object_type,
+                    context,
+                )
+            if direct is not None and not isinstance(
+                get_proper_type(direct[0]), (UnionType, AnyType)
+            ):
+                # We only return non-unions soon, to avoid greedy match.
+                return [direct]
 
         # Step 4: Split the first remaining union type in arguments into items and
         # try to match each item individually (recursive).
@@ -2729,6 +2780,7 @@ def union_overload_result(
                 arg_names,
                 callable_name,
                 object_type,
+                none_type_var_overlap,
                 context,
                 level + 1,
             )
diff --git a/mypy/subtypes.py b/mypy/subtypes.py
index 5712d7375e50..da92f7398d4e 100644
--- a/mypy/subtypes.py
+++ b/mypy/subtypes.py
@@ -1299,6 +1299,7 @@ def is_callable_compatible(
     check_args_covariantly: bool = False,
     allow_partial_overlap: bool = False,
     strict_concatenate: bool = False,
+    no_unify_none: bool = False,
 ) -> bool:
     """Is the left compatible with the right, using the provided compatibility check?
 
@@ -1415,7 +1416,9 @@ def g(x: int) -> int: ...
     # (below) treats type variables on the two sides as independent.
     if left.variables:
         # Apply generic type variables away in left via type inference.
-        unified = unify_generic_callable(left, right, ignore_return=ignore_return)
+        unified = unify_generic_callable(
+            left, right, ignore_return=ignore_return, no_unify_none=no_unify_none
+        )
         if unified is None:
             return False
         left = unified
@@ -1427,7 +1430,9 @@ def g(x: int) -> int: ...
     # So, we repeat the above checks in the opposite direction. This also
     # lets us preserve the 'symmetry' property of allow_partial_overlap.
     if allow_partial_overlap and right.variables:
-        unified = unify_generic_callable(right, left, ignore_return=ignore_return)
+        unified = unify_generic_callable(
+            right, left, ignore_return=ignore_return, no_unify_none=no_unify_none
+        )
         if unified is not None:
             right = unified
 
@@ -1687,6 +1692,8 @@ def unify_generic_callable(
     target: NormalizedCallableType,
     ignore_return: bool,
     return_constraint_direction: int | None = None,
+    *,
+    no_unify_none: bool = False,
 ) -> NormalizedCallableType | None:
     """Try to unify a generic callable type with another callable type.
 
@@ -1708,6 +1715,10 @@ def unify_generic_callable(
             type.ret_type, target.ret_type, return_constraint_direction
         )
         constraints.extend(c)
+    if no_unify_none:
+        constraints = [
+            c for c in constraints if not isinstance(get_proper_type(c.target), NoneType)
+        ]
     inferred_vars, _ = mypy.solve.solve_constraints(type.variables, constraints)
     if None in inferred_vars:
         return None
diff --git a/test-data/unit/check-overloading.test b/test-data/unit/check-overloading.test
index 50acd7d77c8c..4910dfe05d31 100644
--- a/test-data/unit/check-overloading.test
+++ b/test-data/unit/check-overloading.test
@@ -2185,36 +2185,63 @@ def bar2(*x: int) -> int: ...
 [builtins fixtures/tuple.pyi]
 
 [case testOverloadDetectsPossibleMatchesWithGenerics]
-from typing import overload, TypeVar, Generic
+# flags: --strict-optional
+from typing import overload, TypeVar, Generic, Optional, List
 
 T = TypeVar('T')
+# The examples below are unsafe, but it is a quite common pattern
+# so we ignore the possibility of type variables taking value `None`
+# for the purpose of overload overlap checks.
 
 @overload
-def foo(x: None, y: None) -> str: ...  # E: Overloaded function signatures 1 and 2 overlap with incompatible return types
+def foo(x: None, y: None) -> str: ...
 @overload
 def foo(x: T, y: T) -> int: ...
 def foo(x): ...
 
+oi: Optional[int]
+reveal_type(foo(None, None))  # N: Revealed type is "builtins.str"
+reveal_type(foo(None, 42))  # N: Revealed type is "builtins.int"
+reveal_type(foo(42, 42))  # N: Revealed type is "builtins.int"
+reveal_type(foo(oi, None))  # N: Revealed type is "Union[builtins.int, builtins.str]"
+reveal_type(foo(oi, 42))  # N: Revealed type is "builtins.int"
+reveal_type(foo(oi, oi))  # N: Revealed type is "Union[builtins.int, builtins.str]"
+
+@overload
+def foo_list(x: None) -> None: ...
+@overload
+def foo_list(x: T) -> List[T]: ...
+def foo_list(x): ...
+
+reveal_type(foo_list(oi))  # N: Revealed type is "Union[builtins.list[builtins.int], None]"
+
 # What if 'T' is 'object'?
 @overload
-def bar(x: None, y: int) -> str: ...  # E: Overloaded function signatures 1 and 2 overlap with incompatible return types
+def bar(x: None, y: int) -> str: ...
 @overload
 def bar(x: T, y: T) -> int: ...
 def bar(x, y): ...
 
 class Wrapper(Generic[T]):
     @overload
-    def foo(self, x: None, y: None) -> str: ...  # E: Overloaded function signatures 1 and 2 overlap with incompatible return types
+    def foo(self, x: None, y: None) -> str: ...
     @overload
     def foo(self, x: T, y: None) -> int: ...
     def foo(self, x): ...
 
     @overload
-    def bar(self, x: None, y: int) -> str: ...  # E: Overloaded function signatures 1 and 2 overlap with incompatible return types
+    def bar(self, x: None, y: int) -> str: ...
     @overload
     def bar(self, x: T, y: T) -> int: ...
     def bar(self, x, y): ...
 
+@overload
+def baz(x: str, y: str) -> str: ...  # E: Overloaded function signatures 1 and 2 overlap with incompatible return types
+@overload
+def baz(x: T, y: T) -> int: ...
+def baz(x): ...
+[builtins fixtures/tuple.pyi]
+
 [case testOverloadFlagsPossibleMatches]
 from wrapper import *
 [file wrapper.pyi]
@@ -3996,7 +4023,7 @@ T = TypeVar('T')
 
 class FakeAttribute(Generic[T]):
     @overload
-    def dummy(self, instance: None, owner: Type[T]) -> 'FakeAttribute[T]': ...  # E: Overloaded function signatures 1 and 2 overlap with incompatible return types
+    def dummy(self, instance: None, owner: Type[T]) -> 'FakeAttribute[T]': ...
     @overload
     def dummy(self, instance: T, owner: Type[T]) -> int: ...
     def dummy(self, instance: Optional[T], owner: Type[T]) -> Union['FakeAttribute[T]', int]: ...