diff --git a/pandas/core/dtypes/cast.py b/pandas/core/dtypes/cast.py
index 16987d4e4492f7..7147e004330404 100644
--- a/pandas/core/dtypes/cast.py
+++ b/pandas/core/dtypes/cast.py
@@ -1909,13 +1909,19 @@ def maybe_unbox_datetimelike_tz_deprecation(
     along with a timezone-naive datetime64 dtype, which is deprecated.
     """
     # Caller is responsible for checking dtype.kind in ["m", "M"]
+
+    if isinstance(value, datetime):
+        # we dont want to box dt64, in particular datetime64("NaT")
+        value = maybe_box_datetimelike(value, dtype)
+
     try:
         value = maybe_unbox_datetimelike(value, dtype)
     except TypeError:
         if (
             isinstance(value, Timestamp)
-            and value.tz is not None
+            and value.tzinfo is not None
             and isinstance(dtype, np.dtype)
+            and dtype.kind == "M"
         ):
             warnings.warn(
                 "Data is timezone-aware. Converting "
diff --git a/pandas/tests/frame/test_constructors.py b/pandas/tests/frame/test_constructors.py
index f04809d9d8832c..d271cf99b165cf 100644
--- a/pandas/tests/frame/test_constructors.py
+++ b/pandas/tests/frame/test_constructors.py
@@ -2509,10 +2509,13 @@ def test_construction_preserves_tzaware_dtypes(self, tz):
         )
         tm.assert_series_equal(result, expected)
 
-    def test_constructor_data_aware_dtype_naive(self, tz_aware_fixture):
+    @pytest.mark.parametrize("pydt", [True, False])
+    def test_constructor_data_aware_dtype_naive(self, tz_aware_fixture, pydt):
         # GH#25843, GH#41555, GH#33401
         tz = tz_aware_fixture
         ts = Timestamp("2019", tz=tz)
+        if pydt:
+            ts = ts.to_pydatetime()
         ts_naive = Timestamp("2019")
 
         with tm.assert_produces_warning(FutureWarning):
diff --git a/pandas/tests/series/test_constructors.py b/pandas/tests/series/test_constructors.py
index 41c0cbf58e438d..8b1f268896240d 100644
--- a/pandas/tests/series/test_constructors.py
+++ b/pandas/tests/series/test_constructors.py
@@ -1535,10 +1535,13 @@ def test_constructor_tz_mixed_data(self):
         expected = Series(dt_list, dtype=object)
         tm.assert_series_equal(result, expected)
 
-    def test_constructor_data_aware_dtype_naive(self, tz_aware_fixture):
+    @pytest.mark.parametrize("pydt", [True, False])
+    def test_constructor_data_aware_dtype_naive(self, tz_aware_fixture, pydt):
         # GH#25843, GH#41555, GH#33401
         tz = tz_aware_fixture
         ts = Timestamp("2019", tz=tz)
+        if pydt:
+            ts = ts.to_pydatetime()
         ts_naive = Timestamp("2019")
 
         with tm.assert_produces_warning(FutureWarning, check_stacklevel=False):