BUG: Assigning boolean series with logical indexer

pandas/core/dtypes/cast.py

@@ -1918,7 +1918,13 @@ def np_can_hold_element(dtype: np.dtype, element: Any) -> Any:
                         # i.e. there are pd.NA elements
                         raise LossySetitemError
                 return element
+            # GH 57338
+            # Check boolean array set as object type
+            if tipo.kind == "O" and isinstance(element, np.ndarray):
+                if all(lib.is_bool(e) for e in element):
+                    return element.astype("bool")
             raise LossySetitemError
+
         if lib.is_bool(element):
             return element
         raise LossySetitemError

pandas/tests/dtypes/cast/test_can_hold_element.py

@@ -77,3 +77,17 @@ def test_can_hold_element_int8_int():
     assert not can_hold_element(arr, np.uint32(element))
     assert not can_hold_element(arr, np.int64(element))
     assert not can_hold_element(arr, np.uint64(element))
+
+
+def test_can_hold_element_bool():
+    arr = np.array([], dtype=bool)
+
+    element = True
+    assert can_hold_element(arr, element)
+    assert can_hold_element(arr, np.array([element]))
+    assert can_hold_element(arr, np.array([element], dtype=object))
+
+    element = 1
+    assert not can_hold_element(arr, element)
+    assert not can_hold_element(arr, np.array([element]))
+    assert not can_hold_element(arr, np.array([element], dtype=object))