diff --git a/pandas/core/dtypes/base.py b/pandas/core/dtypes/base.py
index 6b00a5284ec5b..c6386db82c23e 100644
--- a/pandas/core/dtypes/base.py
+++ b/pandas/core/dtypes/base.py
@@ -65,6 +65,7 @@ class ExtensionDtype:
     * _is_numeric
     * _is_boolean
     * _get_common_dtype
+    * _find_compatible_dtype
 
     The `na_value` class attribute can be used to set the default NA value
     for this type. :attr:`numpy.nan` is used by default.
@@ -445,6 +446,25 @@ def _can_fast_transpose(self) -> bool:
         """
         return False
 
+    def _find_compatible_dtype(self, item: Any) -> tuple[DtypeObj, Any]:
+        """
+        Find the minimal dtype that we need to upcast to in order to hold
+        the given item.
+
+        This is used in when doing Series setitem-with-expansion on a Series
+        with our dtype.
+
+        Parameters
+        ----------
+        item : object
+
+        Returns
+        -------
+        np.dtype or ExtensionDtype
+        object
+        """
+        return np.dtype(object), item
+
 
 class StorageExtensionDtype(ExtensionDtype):
     """ExtensionDtype that may be backed by more than one implementation."""
diff --git a/pandas/core/dtypes/cast.py b/pandas/core/dtypes/cast.py
index 320f028f4484c..3a104f5719148 100644
--- a/pandas/core/dtypes/cast.py
+++ b/pandas/core/dtypes/cast.py
@@ -50,7 +50,6 @@
     ensure_int16,
     ensure_int32,
     ensure_int64,
-    ensure_object,
     ensure_str,
     is_bool,
     is_complex,
@@ -548,13 +547,13 @@ def ensure_dtype_can_hold_na(dtype: DtypeObj) -> DtypeObj:
 }
 
 
-def maybe_promote(dtype: np.dtype, fill_value=np.nan):
+def maybe_promote(dtype: DtypeObj, fill_value=np.nan):
     """
     Find the minimal dtype that can hold both the given dtype and fill_value.
 
     Parameters
     ----------
-    dtype : np.dtype
+    dtype : np.dtype or ExtensionDtype
     fill_value : scalar, default np.nan
 
     Returns
@@ -611,9 +610,13 @@ def _maybe_promote_cached(dtype, fill_value, fill_value_type):
     return _maybe_promote(dtype, fill_value)
 
 
-def _maybe_promote(dtype: np.dtype, fill_value=np.nan):
+def _maybe_promote(dtype: DtypeObj, fill_value=np.nan):
     # The actual implementation of the function, use `maybe_promote` above for
     # a cached version.
+
+    if not isinstance(dtype, np.dtype):
+        return dtype._find_compatible_dtype(fill_value)
+
     if not is_scalar(fill_value):
         # with object dtype there is nothing to promote, and the user can
         #  pass pretty much any weird fill_value they like
@@ -629,12 +632,6 @@ def _maybe_promote(dtype: np.dtype, fill_value=np.nan):
         fv = na_value_for_dtype(dtype)
         return dtype, fv
 
-    elif isinstance(dtype, CategoricalDtype):
-        if fill_value in dtype.categories or isna(fill_value):
-            return dtype, fill_value
-        else:
-            return object, ensure_object(fill_value)
-
     elif isna(fill_value):
         dtype = _dtype_obj
         if fill_value is None:
diff --git a/pandas/core/dtypes/dtypes.py b/pandas/core/dtypes/dtypes.py
index 07fb25008cfb2..3a9d953d39004 100644
--- a/pandas/core/dtypes/dtypes.py
+++ b/pandas/core/dtypes/dtypes.py
@@ -686,6 +686,15 @@ def index_class(self) -> type_t[CategoricalIndex]:
 
         return CategoricalIndex
 
+    def _find_compatible_dtype(self, item) -> tuple[DtypeObj, Any]:
+        from pandas.core.dtypes.missing import is_valid_na_for_dtype
+
+        if item in self.categories or is_valid_na_for_dtype(
+            item, self.categories.dtype
+        ):
+            return self, item
+        return np.dtype(object), item
+
 
 @register_extension_dtype
 class DatetimeTZDtype(PandasExtensionDtype):
@@ -1606,6 +1615,18 @@ def _get_common_dtype(self, dtypes: list[DtypeObj]) -> DtypeObj | None:
         except (KeyError, NotImplementedError):
             return None
 
+    def _find_compatible_dtype(self, item) -> tuple[DtypeObj, Any]:
+        from pandas.core.dtypes.cast import maybe_promote
+        from pandas.core.dtypes.missing import is_valid_na_for_dtype
+
+        if is_valid_na_for_dtype(item, self):
+            return self, item
+
+        dtype, item = maybe_promote(self.numpy_dtype, item)
+        if dtype.kind in "iufb":
+            return type(self).from_numpy_dtype(dtype), item
+        return dtype, item
+
 
 @register_extension_dtype
 class SparseDtype(ExtensionDtype):
@@ -2344,3 +2365,29 @@ def __from_arrow__(self, array: pa.Array | pa.ChunkedArray):
         array_class = self.construct_array_type()
         arr = array.cast(self.pyarrow_dtype, safe=True)
         return array_class(arr)
+
+    def _find_compatible_dtype(self, item: Any) -> tuple[DtypeObj, Any]:
+        if isinstance(item, pa.Scalar):
+            if not item.is_valid:
+                # TODO: ask joris for help making these checks more robust
+                if item.type == self.pyarrow_dtype:
+                    return self, item.as_py()
+                if item.type.to_pandas_dtype() == np.int64 and self.kind == "i":
+                    # FIXME: kludge
+                    return self, item.as_py()
+
+            item = item.as_py()
+
+        elif item is None or item is libmissing.NA:
+            # TODO: np.nan? use is_valid_na_for_dtype
+            return self, item
+
+        from pandas.core.dtypes.cast import maybe_promote
+
+        dtype, item = maybe_promote(self.numpy_dtype, item)
+
+        if dtype == self.numpy_dtype:
+            return self, item
+
+        # TODO: implement from_numpy_dtype analogous to MaskedDtype.from_numpy_dtype
+        return np.dtype(object), item
diff --git a/pandas/core/indexing.py b/pandas/core/indexing.py
index e3928621a4e48..62dc8cc793f46 100644
--- a/pandas/core/indexing.py
+++ b/pandas/core/indexing.py
@@ -56,12 +56,7 @@
     ABCDataFrame,
     ABCSeries,
 )
-from pandas.core.dtypes.missing import (
-    infer_fill_value,
-    is_valid_na_for_dtype,
-    isna,
-    na_value_for_dtype,
-)
+from pandas.core.dtypes.missing import infer_fill_value
 
 from pandas.core import algorithms as algos
 import pandas.core.common as com
@@ -2203,26 +2198,14 @@ def _setitem_with_indexer_missing(self, indexer, value):
                     return self._setitem_with_indexer(new_indexer, value, "loc")
 
             # this preserves dtype of the value and of the object
-            if not is_scalar(value):
-                new_dtype = None
-
-            elif is_valid_na_for_dtype(value, self.obj.dtype):
-                if not is_object_dtype(self.obj.dtype):
-                    # Every NA value is suitable for object, no conversion needed
-                    value = na_value_for_dtype(self.obj.dtype, compat=False)
-
-                new_dtype = maybe_promote(self.obj.dtype, value)[0]
-
-            elif isna(value):
-                new_dtype = None
+            new_dtype = None
+            if is_list_like(value):
+                pass
             elif not self.obj.empty and not is_object_dtype(self.obj.dtype):
                 # We should not cast, if we have object dtype because we can
                 # set timedeltas into object series
                 curr_dtype = self.obj.dtype
-                curr_dtype = getattr(curr_dtype, "numpy_dtype", curr_dtype)
-                new_dtype = maybe_promote(curr_dtype, value)[0]
-            else:
-                new_dtype = None
+                new_dtype, value = maybe_promote(curr_dtype, value)
 
             new_values = Series([value], dtype=new_dtype)._values
 
diff --git a/pandas/tests/extension/decimal/array.py b/pandas/tests/extension/decimal/array.py
index 9ce7ac309b6d3..19a085c4fe2e8 100644
--- a/pandas/tests/extension/decimal/array.py
+++ b/pandas/tests/extension/decimal/array.py
@@ -65,6 +65,14 @@ def construct_array_type(cls) -> type_t[DecimalArray]:
     def _is_numeric(self) -> bool:
         return True
 
+    def _find_compatible_dtype(self, item):
+        if isinstance(item, decimal.Decimal):
+            # TODO: need to watch out for precision?
+            # TODO: allow non-decimal numeric?
+            # TODO: allow np.nan, pd.NA?
+            return (self, item)
+        return (np.dtype(object), item)
+
 
 class DecimalArray(OpsMixin, ExtensionScalarOpsMixin, ExtensionArray):
     __array_priority__ = 1000
diff --git a/pandas/tests/extension/decimal/test_decimal.py b/pandas/tests/extension/decimal/test_decimal.py
index 5ccffd1d25b3d..562d97f739ae1 100644
--- a/pandas/tests/extension/decimal/test_decimal.py
+++ b/pandas/tests/extension/decimal/test_decimal.py
@@ -535,3 +535,12 @@ def test_array_copy_on_write(using_copy_on_write):
             {"a": [decimal.Decimal(2), decimal.Decimal(3)]}, dtype=DecimalDtype()
         )
         tm.assert_equal(df2.values, expected.values)
+
+
+def test_setitem_with_expansion():
+    # GH#32346 dont upcast to object
+    arr = DecimalArray(make_data())
+    ser = pd.Series(arr[:3])
+
+    ser[3] = ser[0]
+    assert ser.dtype == arr.dtype
diff --git a/pandas/tests/extension/test_arrow.py b/pandas/tests/extension/test_arrow.py
index 1941e359299b6..060e6a3c93c6a 100644
--- a/pandas/tests/extension/test_arrow.py
+++ b/pandas/tests/extension/test_arrow.py
@@ -2751,6 +2751,29 @@ def test_describe_timedelta_data(pa_type):
     tm.assert_series_equal(result, expected)
 
 
+@pytest.mark.parametrize(
+    "value, target_value, dtype",
+    [
+        (pa.scalar(4, type="int32"), 4, "int32[pyarrow]"),
+        (pa.scalar(4, type="int64"), 4, "int32[pyarrow]"),
+        # (pa.scalar(4.5, type="float64"), 4, "int32[pyarrow]"),
+        (4, 4, "int32[pyarrow]"),
+        (pd.NA, None, "int32[pyarrow]"),
+        (None, None, "int32[pyarrow]"),
+        (pa.scalar(None, type="int32"), None, "int32[pyarrow]"),
+        (pa.scalar(None, type="int64"), None, "int32[pyarrow]"),
+    ],
+)
+def test_series_setitem_with_enlargement(value, target_value, dtype):
+    # GH#52235
+    # similar to series/inedexing/test_setitem.py::test_setitem_keep_precision
+    # and test_setitem_enlarge_with_na, but for arrow dtypes
+    ser = pd.Series([1, 2, 3], dtype=dtype)
+    ser[3] = value
+    expected = pd.Series([1, 2, 3, target_value], dtype=dtype)
+    tm.assert_series_equal(ser, expected)
+
+
 @pytest.mark.parametrize("pa_type", tm.DATETIME_PYARROW_DTYPES)
 def test_describe_datetime_data(pa_type):
     # GH53001
diff --git a/pandas/tests/indexing/test_loc.py b/pandas/tests/indexing/test_loc.py
index ce7dde3c4cb42..b026b59502f43 100644
--- a/pandas/tests/indexing/test_loc.py
+++ b/pandas/tests/indexing/test_loc.py
@@ -1994,6 +1994,28 @@ def test_loc_drops_level(self):
 
 
 class TestLocSetitemWithExpansion:
+    def test_series_loc_setitem_with_expansion_categorical(self):
+        # NA value that can't be held in integer categories
+        ser = Series([1, 2, 3], dtype="category")
+        ser.loc[3] = pd.NaT
+        assert ser.dtype == object
+
+    def test_series_loc_setitem_with_expansion_interval(self):
+        idx = pd.interval_range(1, 3)
+        ser2 = Series(idx)
+        ser2.loc[2] = np.nan
+        assert ser2.dtype == "interval[float64, right]"
+
+        ser2.loc[3] = pd.NaT
+        assert ser2.dtype == object
+
+    def test_series_loc_setitem_with_expansion_list_object(self):
+        ser3 = Series(range(3))
+        ser3.loc[3] = []
+        assert ser3.dtype == object
+        item = ser3.loc[3]
+        assert isinstance(item, list) and len(item) == 0
+
     def test_loc_setitem_with_expansion_large_dataframe(self, monkeypatch):
         # GH#10692
         size_cutoff = 50
diff --git a/pandas/tests/series/indexing/test_setitem.py b/pandas/tests/series/indexing/test_setitem.py
index e583d55101a8b..b77473e7fc9ef 100644
--- a/pandas/tests/series/indexing/test_setitem.py
+++ b/pandas/tests/series/indexing/test_setitem.py
@@ -621,7 +621,10 @@ def test_setitem_enlargement_object_none(self, nulls_fixture, using_infer_string
         )
         expected = Series(["a", "b", nulls_fixture], index=[0, 1, 3], dtype=dtype)
         tm.assert_series_equal(ser, expected)
-        if using_infer_string:
+        if isinstance(nulls_fixture, float):
+            # We retain the same type, but maybe not the same _object_
+            assert np.isnan(ser[3])
+        elif using_infer_string:
             ser[3] is np.nan
         else:
             assert ser[3] is nulls_fixture