Add test for nontick offsets with ambiguous time error

Author: jackzyliu

pandas/tests/tseries/offsets/test_dst.py

@@ -4,6 +4,7 @@
 from datetime import timedelta
 
 import pytest
+import pytz
 
 from pandas._libs.tslibs import Timestamp
 from pandas._libs.tslibs.offsets import (
@@ -15,6 +16,7 @@
     BYearEnd,
     CBMonthBegin,
     CBMonthEnd,
+    CustomBusinessDay,
     DateOffset,
     Day,
     MonthBegin,
@@ -173,3 +175,48 @@ def test_all_offset_classes(self, tup):
         first = Timestamp(test_values[0], tz="US/Eastern") + offset()
         second = Timestamp(test_values[1], tz="US/Eastern")
         assert first == second
+
+
+@pytest.mark.parametrize(
+    "original_dt, target_dt, offset, tz",
+    [
+        (
+            Timestamp("1900-01-01"),
+            Timestamp("1905-07-01"),
+            MonthBegin(66),
+            "Africa/Kinshasa",
+        ),  # GH41906
+        (
+            Timestamp("2021-10-01 01:15"),
+            Timestamp("2021-10-31 01:15"),
+            MonthEnd(1),
+            "Europe/London",
+        ),
+        (
+            Timestamp("2010-12-05 02:59"),
+            Timestamp("2010-10-31 02:59"),
+            SemiMonthEnd(-3),
+            "Europe/Paris",
+        ),
+        (
+            Timestamp("2021-10-31 01:20"),
+            Timestamp("2021-11-07 01:20"),
+            CustomBusinessDay(2, weekmask="Sun Mon"),
+            "US/Eastern",
+        ),
+        (
+            Timestamp("2020-04-03 01:30"),
+            Timestamp("2020-11-01 01:30"),
+            YearBegin(1, month=11),
+            "America/Chicago",
+        ),
+    ],
+)
+def test_nontick_offset_with_ambiguous_time_error(original_dt, target_dt, offset, tz):
+    # .apply for non-Tick offsets throws AmbiguousTimeError when the target dt
+    # is dst-ambiguous
+    localized_dt = original_dt.tz_localize(tz)
+
+    msg = f"Cannot infer dst time from {target_dt}, try using the 'ambiguous' argument"
+    with pytest.raises(pytz.AmbiguousTimeError, match=msg):
+        localized_dt + offset