diff --git a/mypy/constraints.py b/mypy/constraints.py
index aa095316c234..749e0dcab499 100644
--- a/mypy/constraints.py
+++ b/mypy/constraints.py
@@ -342,7 +342,9 @@ def _infer_constraints(
     # checkexpr.has_erased_component().
     if not type_state.keep_unions and isinstance(template, UnionType):
         template = mypy.typeops.make_simplified_union(template.items, keep_erased=True)
+    unsimplified_actual: UnionType | None = None
     if not type_state.keep_unions and isinstance(actual, UnionType):
+        unsimplified_actual = actual
         actual = mypy.typeops.make_simplified_union(actual.items, keep_erased=True)
 
     # Ignore Any types from the type suggestion engine to avoid them
@@ -428,13 +430,16 @@ def _infer_constraints(
         # We infer constraints eagerly -- try to find constraints for a type
         # variable if possible. This seems to help with some real-world
         # use cases.
-        return any_constraints(
-            [
-                infer_constraints_if_possible(template, a_item, direction)
-                for a_item in actual.items
-            ],
-            eager=True,
-        )
+        options = [
+            infer_constraints_if_possible(template, a_item, direction) for a_item in actual.items
+        ]
+        if unsimplified_actual is not None:
+            options.extend(
+                _options_lost_by_simplification(
+                    template, actual.items, options, unsimplified_actual.items
+                )
+            )
+        return any_constraints(options, eager=True)
     if direction == SUPERTYPE_OF and isinstance(template, UnionType):
         # When the template is a union, we are okay with leaving some
         # type variables indeterminate. This helps with some special
@@ -476,6 +481,51 @@ def _unwrap_type_type(tp: TypeType | UnionType) -> ProperType:
     return UnionType.make_union([cast(TypeType, get_proper_type(o)).item for o in tp.items])
 
 
+def _options_lost_by_simplification(
+    template: ProperType,
+    simplified_items: Sequence[Type],
+    simplified_options: list[list[Constraint] | None],
+    original_items: Sequence[Type],
+) -> list[list[Constraint] | None]:
+    """Constraint options for union items dropped by simplification that we still need.
+
+    Simplification drops an item X when it is a proper subtype of another item Y,
+    but subtyping is not always transitive through the template: ``MutableSequence[str]``
+    is a subtype of ``Hashable``, yet ``list[str]`` is not hashable even though it is
+    a subtype of ``MutableSequence[str]``. If the template can match X but none of the
+    items that absorbed X can, keep X as an extra option so the solver does not commit
+    to a wrong member (e.g. inferring ``T = bool`` from ``list[bool]`` alone).
+    """
+    # Only recover an option when some simplified item already produced
+    # constraints: recovery exists to offer an alternative to a (possibly
+    # wrong) commitment, not to invent constraints where the fallback --
+    # inferring the literal's type from its items -- already applies. Without
+    # this, a context like ``Hashable | Sequence[Hashable] |
+    # dict[Hashable, Hashable]`` would gain a ``T = Hashable`` constraint for
+    # ``[names]`` and report a new ``list-item`` error where previously only
+    # an ``assignment`` error was reported (pandas/core/indexes/base.py:2143,
+    # reported by mypy_primer on #22381).
+    if not any(option is not None for option in simplified_options):
+        return []
+    simplified_ids = {id(get_proper_type(item)) for item in simplified_items}
+    extra: list[list[Constraint] | None] = []
+    for item in original_items:
+        proper_item = get_proper_type(item)
+        if id(proper_item) in simplified_ids or isinstance(proper_item, UnionType):
+            continue
+        absorbers = [
+            option
+            for simplified_item, option in zip(simplified_items, simplified_options)
+            if mypy.subtypes.is_proper_subtype(item, simplified_item, keep_erased_types=True)
+        ]
+        if not absorbers or any(option is not None for option in absorbers):
+            continue
+        option = infer_constraints_if_possible(template, item, SUBTYPE_OF)
+        if option is not None:
+            extra.append(option)
+    return extra
+
+
 def infer_constraints_if_possible(
     template: Type, actual: Type, direction: int
 ) -> list[Constraint] | None:
diff --git a/test-data/unit/check-inference-context.test b/test-data/unit/check-inference-context.test
index 53705ee43be1..888d47c58145 100644
--- a/test-data/unit/check-inference-context.test
+++ b/test-data/unit/check-inference-context.test
@@ -1680,3 +1680,31 @@ x: Union[B, C]
 fn: Callable[[Union[A, B]], None]
 fn = make(x)
 reveal_type(fn)  # N: Revealed type is "def (__main__.B | __main__.C | __main__.A)"
+
+[case testListLiteralContextWithUnhashableListAndHashableSequence]
+# https://github.com/python/mypy/issues/22342
+from typing import Hashable, MutableSequence
+
+def f(k: list[bool] | Hashable | MutableSequence[str]) -> None: ...
+
+f(["a", "b"])
+f([True])
+f([1.5])  # E: Argument 1 to "f" has incompatible type "list[float]"; expected "list[bool] | Hashable | MutableSequence[str]" \
+          # N: Following member(s) of "list[float]" have conflicts: \
+          # N:     __hash__: expected "Callable[[], int]", got "None"
+[builtins fixtures/list_hashable.pyi]
+[typing fixtures/typing-full.pyi]
+
+[case testListLiteralContextUnionWithUnhashableDictMember]
+# mypy_primer regression reported on #22381 for the #22342 fix: no simplified
+# union item yields constraints here, so no option may be recovered. The list
+# literal must keep the previous behaviour (an `assignment` error, which the
+# pandas code suppresses with `# type: ignore[assignment]`), not a new
+# `list-item` error.
+from typing import Hashable, Sequence
+
+def g(names: Hashable | Sequence[Hashable] | dict[Hashable, Hashable]) -> None:
+    names = [names]  # E: Incompatible types in assignment (expression has type "list[Hashable | Sequence[Hashable] | dict[Hashable, Hashable]]", variable has type "Hashable | Sequence[Hashable] | dict[Hashable, Hashable]")
+
+[builtins fixtures/list_hashable.pyi]
+[typing fixtures/typing-full.pyi]
diff --git a/test-data/unit/fixtures/list_hashable.pyi b/test-data/unit/fixtures/list_hashable.pyi
new file mode 100644
index 000000000000..d5ca48057ace
--- /dev/null
+++ b/test-data/unit/fixtures/list_hashable.pyi
@@ -0,0 +1,47 @@
+# Builtins stub used in list tests that need hashability information.
+
+import types
+from typing import Any, ClassVar, Generic, Iterable, Iterator, MutableSequence, TypeVar, overload
+
+T = TypeVar('T')
+
+class object:
+    def __init__(self) -> None: pass
+    def __eq__(self, other: object) -> bool: pass
+    def __hash__(self) -> int: pass
+
+class type: pass
+
+class list(MutableSequence[T]):
+    __hash__: ClassVar[None]  # type: ignore[assignment]
+    @overload
+    def __init__(self) -> None: pass
+    @overload
+    def __init__(self, x: Iterable[T]) -> None: pass
+    def __iter__(self) -> Iterator[T]: pass
+    def __len__(self) -> int: pass
+    def __contains__(self, item: object) -> bool: pass
+    def __add__(self, x: list[T]) -> list[T]: pass
+    def __mul__(self, x: int) -> list[T]: pass
+    def __getitem__(self, x: Any) -> T: pass
+    def __setitem__(self, x: Any, v: T) -> None: pass
+    def append(self, x: T) -> None: pass
+    def extend(self, x: Iterable[T]) -> None: pass
+
+class tuple(Generic[T]): pass
+class function: pass
+class int:
+    def __bool__(self) -> bool: pass
+class float:
+    def __bool__(self) -> bool: pass
+class str:
+    def __len__(self) -> bool: pass
+class bool(int): pass
+
+property = object() # Dummy definition.
+
+K = TypeVar('K')
+V = TypeVar('V')
+
+class dict(Generic[K, V]):
+    __hash__: ClassVar[None]  # type: ignore[assignment]