BUG: Negative freq in date_range produces values out of start and endpoints

pandas/core/arrays/datetimes.py

@@ -2790,7 +2790,12 @@ def _generate_range(
     if start and not offset.is_on_offset(start):
         # Incompatible types in assignment (expression has type "datetime",
         # variable has type "Optional[Timestamp]")
-        start = offset.rollforward(start)  # type: ignore[assignment]
+
+        # GH #56147 account for negative direction and range bounds
+        if offset.n >= 0:
+            start = offset.rollforward(start)  # type: ignore[assignment]
+        else:
+            start = offset.rollback(start)  # type: ignore[assignment]
 
     # Unsupported operand types for < ("Timestamp" and "None")
     if periods is None and end < start and offset.n >= 0:  # type: ignore[operator]

pandas/tests/indexes/datetimes/test_date_range.py

@@ -1729,3 +1729,18 @@ def test_date_range_partial_day_year_end(self, unit):
             freq="YE",
         )
         tm.assert_index_equal(rng, exp)
+
+    def test_date_range_negative_freq_year_end_inbounds(self, unit):
+        # GH#56147
+        rng = date_range(
+            start="2023-10-31 00:00:00",
+            end="2021-10-31 00:00:00",
+            freq="-1YE",
+            unit=unit,
+        )
+        exp = DatetimeIndex(
+            ["2022-12-31 00:00:00", "2021-12-31 00:00:00"],
+            dtype=f"M8[{unit}]",
+            freq="-1YE",
+        )
+        tm.assert_index_equal(rng, exp)