diff --git a/polars/polars-lazy/polars-plan/src/dsl/function_expr/temporal.rs b/polars/polars-lazy/polars-plan/src/dsl/function_expr/temporal.rs
index 9720c3041f74..6e695732a52f 100644
--- a/polars/polars-lazy/polars-plan/src/dsl/function_expr/temporal.rs
+++ b/polars/polars-lazy/polars-plan/src/dsl/function_expr/temporal.rs
@@ -8,11 +8,13 @@ use super::*;
 
 #[cfg(feature = "date_offset")]
 pub(super) fn date_offset(s: Series, offset: Duration) -> PolarsResult<Series> {
+    let preserve_sortedness: bool;
     let out = match s.dtype().clone() {
         DataType::Date => {
             let s = s
                 .cast(&DataType::Datetime(TimeUnit::Milliseconds, None))
                 .unwrap();
+            preserve_sortedness = true;
             date_offset(s, offset).and_then(|s| s.cast(&DataType::Date))
         }
         DataType::Datetime(tu, tz) => {
@@ -37,16 +39,25 @@ pub(super) fn date_offset(s: Series, offset: Duration) -> PolarsResult<Series> {
                     ca.0.try_apply(|v| offset_fn(&offset, v, None))
                 }
             }?;
+            // Sortedness may not be preserved when crossing daylight savings time boundaries
+            // for calendar-aware durations.
+            // Constant durations (e.g. 2 hours) always preserve sortedness.
+            preserve_sortedness =
+                tz.is_none() || tz.as_deref() == Some("UTC") || offset.is_constant_duration();
             out.cast(&DataType::Datetime(tu, tz))
         }
         dt => polars_bail!(
             ComputeError: "cannot use 'date_offset' on Series of datatype {}", dt,
         ),
     };
-    out.map(|mut out| {
-        out.set_sorted_flag(s.is_sorted_flag());
+    if preserve_sortedness {
+        out.map(|mut out| {
+            out.set_sorted_flag(s.is_sorted_flag());
+            out
+        })
+    } else {
         out
-    })
+    }
 }
 
 pub(super) fn combine(s: &[Series], tu: TimeUnit) -> PolarsResult<Series> {
diff --git a/polars/polars-time/src/windows/duration.rs b/polars/polars-time/src/windows/duration.rs
index 2686c6bc73cb..e6c11e4701ae 100644
--- a/polars/polars-time/src/windows/duration.rs
+++ b/polars/polars-time/src/windows/duration.rs
@@ -338,6 +338,10 @@ impl Duration {
         self.days
     }
 
+    pub fn is_constant_duration(&self) -> bool {
+        self.months == 0 && self.weeks == 0 && self.days == 0
+    }
+
     /// Returns the nanoseconds from the `Duration` without the weeks or months part.
     pub fn nanoseconds(&self) -> i64 {
         self.nsecs
diff --git a/py-polars/tests/unit/namespaces/test_datetime.py b/py-polars/tests/unit/namespaces/test_datetime.py
index ecb76458870d..fb528381da62 100644
--- a/py-polars/tests/unit/namespaces/test_datetime.py
+++ b/py-polars/tests/unit/namespaces/test_datetime.py
@@ -139,6 +139,32 @@ def test_local_time_sortedness(time_zone: str | None) -> None:
     assert result.flags["SORTED_DESC"] is False
 
 
+@pytest.mark.parametrize(
+    ("time_zone", "offset", "expected"),
+    [
+        (None, "1d", True),
+        ("Asia/Kathmandu", "1d", False),
+        ("UTC", "1d", True),
+        (None, "1mo", True),
+        ("Asia/Kathmandu", "1mo", False),
+        ("UTC", "1mo", True),
+        (None, "1w", True),
+        ("Asia/Kathmandu", "1w", False),
+        ("UTC", "1w", True),
+        (None, "1h", True),
+        ("Asia/Kathmandu", "1h", True),
+        ("UTC", "1h", True),
+    ],
+)
+def test_offset_by_sortedness(
+    time_zone: str | None, offset: str, expected: bool
+) -> None:
+    ser = (pl.Series([datetime(2022, 1, 1, 23)]).dt.replace_time_zone(time_zone)).sort()
+    result = ser.dt.offset_by(offset)
+    assert result.flags["SORTED_ASC"] == expected
+    assert result.flags["SORTED_DESC"] is False
+
+
 def test_dt_datetime_date_time_invalid() -> None:
     with pytest.raises(ComputeError, match="expected Datetime"):
         pl.Series([date(2021, 1, 2)]).dt.datetime()