diff --git a/doc/source/whatsnew/v1.4.0.rst b/doc/source/whatsnew/v1.4.0.rst
index 24f307f23f435..ba52385ca24a9 100644
--- a/doc/source/whatsnew/v1.4.0.rst
+++ b/doc/source/whatsnew/v1.4.0.rst
@@ -159,7 +159,7 @@ Interval
 Indexing
 ^^^^^^^^
 - Bug in indexing on a :class:`Series` or :class:`DataFrame` with a :class:`DatetimeIndex` when passing a string, the return type depended on whether the index was monotonic (:issue:`24892`)
--
+- Bug in :meth:`DataFrame.truncate` and :meth:`Series.truncate` when the object's Index has a length greater than one but only one unique value (:issue:`42365`)
 
 Missing
 ^^^^^^^
diff --git a/pandas/core/generic.py b/pandas/core/generic.py
index 1abb01099f977..7ea1f0c6216a4 100644
--- a/pandas/core/generic.py
+++ b/pandas/core/generic.py
@@ -9381,7 +9381,7 @@ def truncate(
         if before is not None and after is not None and before > after:
             raise ValueError(f"Truncate: {after} must be after {before}")
 
-        if len(ax) > 1 and ax.is_monotonic_decreasing:
+        if len(ax) > 1 and ax.is_monotonic_decreasing and ax.nunique() > 1:
             before, after = after, before
 
         slicer = [slice(None, None)] * self._AXIS_LEN
diff --git a/pandas/tests/frame/methods/test_truncate.py b/pandas/tests/frame/methods/test_truncate.py
index 210e86067566a..f2d60240009c5 100644
--- a/pandas/tests/frame/methods/test_truncate.py
+++ b/pandas/tests/frame/methods/test_truncate.py
@@ -148,3 +148,13 @@ def test_truncate_multiindex(self, frame_or_series):
             expected = expected["col"]
 
         tm.assert_equal(result, expected)
+
+    def test_truncate_index_only_one_unique_value(self, frame_or_series):
+        # GH 42365
+        obj = Series(0, index=date_range("2021-06-30", "2021-06-30")).repeat(5)
+        if frame_or_series is DataFrame:
+            obj = obj.to_frame(name="a")
+
+        truncated = obj.truncate("2021-06-28", "2021-07-01")
+
+        tm.assert_equal(truncated, obj)
diff --git a/pandas/tests/series/methods/test_truncate.py b/pandas/tests/series/methods/test_truncate.py
index ca5c3e2639097..a3a27a744b180 100644
--- a/pandas/tests/series/methods/test_truncate.py
+++ b/pandas/tests/series/methods/test_truncate.py
@@ -55,3 +55,11 @@ def test_truncate_one_element_series(self):
 
         # the input Series and the expected Series are the same
         tm.assert_series_equal(result, series)
+
+    def test_truncate_index_only_one_unique_value(self):
+        # GH 42365
+        obj = Series(0, index=date_range("2021-06-30", "2021-06-30")).repeat(5)
+
+        truncated = obj.truncate("2021-06-28", "2021-07-01")
+
+        tm.assert_series_equal(truncated, obj)