diff --git a/Doc/library/datetime.rst b/Doc/library/datetime.rst
index 8993049a720b1c..7505028b740b90 100644
--- a/Doc/library/datetime.rst
+++ b/Doc/library/datetime.rst
@@ -1329,9 +1329,11 @@ Supported operations:
 
    Naive and aware :class:`.datetime` objects are never equal.
 
-   If both comparands are aware, and have the same :attr:`!tzinfo` attribute,
-   the :attr:`!tzinfo` and :attr:`~.datetime.fold` attributes are ignored and
-   the base datetimes are compared.
+   If both comparands are aware, and have the same :attr:`!tzinfo` and
+   :attr:`~.datetime.fold` attributes, the base datetimes are compared.
+   If both comparands are aware, and have the same :attr:`!tzinfo` but
+   differing :attr:`~.datetime.fold` attributes, the objects are converted to
+   timestamps, and the timestamps are compared.
    If both comparands are aware and have different :attr:`~.datetime.tzinfo`
    attributes, the comparison acts as comparands were first converted to UTC
    datetimes except that the implementation never overflows.
@@ -1345,9 +1347,11 @@ Supported operations:
    Order comparison between naive and aware :class:`.datetime` objects
    raises :exc:`TypeError`.
 
-   If both comparands are aware, and have the same :attr:`!tzinfo` attribute,
-   the :attr:`!tzinfo` and :attr:`~.datetime.fold` attributes are ignored and
-   the base datetimes are compared.
+   If both comparands are aware, and have the same :attr:`!tzinfo` and
+   :attr:`~.datetime.fold` attributes, the base datetimes are compared.
+   If both comparands are aware, and have the same :attr:`!tzinfo` but
+   differing :attr:`~.datetime.fold` attributes, the objects are converted to
+   timestamps, and the timestamps are compared.
    If both comparands are aware and have different :attr:`~.datetime.tzinfo`
    attributes, the comparison acts as comparands were first converted to UTC
    datetimes except that the implementation never overflows.
@@ -1364,6 +1368,11 @@ Supported operations:
    The default behavior can be changed by overriding the special comparison
    methods in subclasses.
 
+.. versionchanged:: 3.15
+   Comparison between :class:`.datetime` objects with matching :attr:`!tzinfo`
+   and differing :attr:`~.datetime.fold` attributes uses timestamps for
+   comparison, so that ordering is preserved even in the case of a repeated
+   interval.
 
 Instance methods:
 
diff --git a/Lib/_pydatetime.py b/Lib/_pydatetime.py
index b6d68f2372850a..ef2160f0c41bc4 100644
--- a/Lib/_pydatetime.py
+++ b/Lib/_pydatetime.py
@@ -2296,6 +2296,11 @@ def _cmp(self, other, allow_mixed=False):
         myoff = otoff = None
 
         if mytz is ottz:
+            # If the objects' fold properties differ, the `fold=1` timestamp may
+            # follow the `fold=0` timestamp even though fielf-by-field comparison
+            # would otherwise conclude that it occurs before. (#146236)
+            if self.fold != other.fold:
+                return _cmp(self.timestamp(), other.timestamp())
             base_compare = True
         else:
             myoff = self.utcoffset()
diff --git a/Lib/test/datetimetester.py b/Lib/test/datetimetester.py
index e264433ca590bf..dce629e332c6d8 100644
--- a/Lib/test/datetimetester.py
+++ b/Lib/test/datetimetester.py
@@ -15,6 +15,7 @@
 import textwrap
 import unittest
 import warnings
+import zoneinfo
 
 from array import array
 
@@ -5985,6 +5986,20 @@ def test_tricky(self):
                         self.assertEqual(astz.replace(tzinfo=None), expected)
                     asutcbase += HOUR
 
+    @unittest.skipUnless("America/Los_Angeles" in zoneinfo.available_timezones(),
+                         "Can't find timezone database")
+    def test_ordering_dst(self):
+        for utc in utc_real, utc_fake:
+            for tz in zoneinfo.ZoneInfo("America/Los_Angeles"), zoneinfo.ZoneInfo("America/New_York"):
+                print(f"{tz!r} {self.dstoff!r} {utc is utc_fake} {id(datetime)}")
+                tm = tm0 = self.dstoff.replace(tzinfo=tz, hour=0)
+                print(f"{tm0!r}")
+                for h in range(4):
+                    for m in 1, 30, 59:
+                        tm1 = (tm.astimezone(utc) + timedelta(hours=h, minutes=m)).astimezone(tz)
+                        print(f"{tm1!r}")
+                        self.assertLess(tm0, tm1)
+                        tm0 = tm1
 
     def test_bogus_dst(self):
         class ok(tzinfo):
diff --git a/Lib/test/test_zoneinfo/test_zoneinfo.py b/Lib/test/test_zoneinfo/test_zoneinfo.py
index aaab4709464fd0..d550063baaf748 100644
--- a/Lib/test/test_zoneinfo/test_zoneinfo.py
+++ b/Lib/test/test_zoneinfo/test_zoneinfo.py
@@ -389,6 +389,21 @@ def test_folds_from_utc(self):
                     dt_after = dt_after_utc.astimezone(zi)
                     self.assertEqual(dt_after.fold, 1, (dt_after, dt_utc))
 
+
+    def test_ordering_dst(self):
+        UTC = self.klass("UTC")
+        dstoff = datetime(2002, 10, 27, 1)
+        tz = self.klass("America/Los_Angeles")
+        print(f"{tz!r} {dstoff!r} {id(datetime)}")
+        tm = tm0 = dstoff.replace(tzinfo=tz, hour=0)
+        print(f"{tm0!r}")
+        for h in range(4):
+            for m in 1, 30, 59:
+                tm1 = (tm.astimezone(UTC) + timedelta(hours=h, minutes=m)).astimezone(tz)
+                print(f"{tm1!r}")
+                self.assertLess(tm0, tm1)
+                tm0 = tm1
+
     def test_time_variable_offset(self):
         # self.zones() only ever returns variable-offset zones
         for key in self.zones():
diff --git a/Misc/NEWS.d/next/Library/2026-03-21-10-14-35.gh-issue-146236.BB_ShV.rst b/Misc/NEWS.d/next/Library/2026-03-21-10-14-35.gh-issue-146236.BB_ShV.rst
new file mode 100644
index 00000000000000..6e8ca3e176adf1
--- /dev/null
+++ b/Misc/NEWS.d/next/Library/2026-03-21-10-14-35.gh-issue-146236.BB_ShV.rst
@@ -0,0 +1,3 @@
+Comparison of datetime values with ``fold=1`` now compares the objects'
+timestamps so that correct ordering of timestamps is maintained at the end
+of DST.
diff --git a/Modules/_datetimemodule.c b/Modules/_datetimemodule.c
index 9d803dc94b64c7..b88dfb1bda11bf 100644
--- a/Modules/_datetimemodule.c
+++ b/Modules/_datetimemodule.c
@@ -114,6 +114,9 @@ typedef struct {
 #define CONST_EPOCH(st) st->epoch
 #define CONST_UTC(st) ((PyObject *)&utc_timezone)
 
+static PyObject *
+datetime_timestamp(PyObject *op, PyObject *Py_UNUSED(dummy));
+
 static datetime_state *
 get_module_state(PyObject *module)
 {
@@ -6565,6 +6568,18 @@ datetime_richcompare(PyObject *self, PyObject *other, int op)
     }
 
     if (GET_DT_TZINFO(self) == GET_DT_TZINFO(other)) {
+        // If the objects' fold properties differ, the `fold=1` timestamp may
+        // follow the `fold=0` timestamp even though fielf-by-field comparison
+        // would otherwise conclude that it occurs before. (#146236)
+        if (DATE_GET_FOLD(self) != DATE_GET_FOLD(other)) {
+            PyObject *ts_self = datetime_timestamp(self, NULL);
+            PyObject *ts_other = datetime_timestamp(other, NULL);
+            PyObject *result = PyObject_RichCompare(ts_self, ts_other, op);
+            Py_DECREF(ts_self);
+            Py_DECREF(ts_other);
+            return result;
+        }
+
         diff = memcmp(((PyDateTime_DateTime *)self)->data,
                       ((PyDateTime_DateTime *)other)->data,
                       _PyDateTime_DATETIME_DATASIZE);