diff --git a/doc/source/whatsnew/v0.25.0.rst b/doc/source/whatsnew/v0.25.0.rst
index da939687500b6..d18b1a576f30c 100644
--- a/doc/source/whatsnew/v0.25.0.rst
+++ b/doc/source/whatsnew/v0.25.0.rst
@@ -691,6 +691,7 @@ Timezones
 - Bug in :func:`to_datetime` where an uninformative ``RuntimeError`` was raised when passing a naive :class:`Timestamp` with datetime strings with mixed UTC offsets (:issue:`25978`)
 - Bug in :func:`to_datetime` with ``unit='ns'`` would drop timezone information from the parsed argument (:issue:`26168`)
 - Bug in :func:`DataFrame.join` where joining a timezone aware index with a timezone aware column would result in a column of ``NaN`` (:issue:`26335`)
+- Bug in :func:`date_range` where ambiguous or nonexistent start or end times were not handled by the ``ambiguous`` or ``nonexistent`` keywords respectively (:issue:`27088`)
 
 Numeric
 ^^^^^^^
diff --git a/pandas/core/arrays/datetimes.py b/pandas/core/arrays/datetimes.py
index eaa0278da6dc3..6b554ddf25c96 100644
--- a/pandas/core/arrays/datetimes.py
+++ b/pandas/core/arrays/datetimes.py
@@ -433,10 +433,12 @@ def _generate_range(cls, start, end, periods, freq, tz=None,
         if tz is not None:
             # Localize the start and end arguments
             start = _maybe_localize_point(
-                start, getattr(start, 'tz', None), start, freq, tz
+                start, getattr(start, 'tz', None), start, freq, tz,
+                ambiguous, nonexistent
             )
             end = _maybe_localize_point(
-                end, getattr(end, 'tz', None), end, freq, tz
+                end, getattr(end, 'tz', None), end, freq, tz,
+                ambiguous, nonexistent
             )
         if freq is not None:
             # We break Day arithmetic (fixed 24 hour) here and opt for
@@ -2121,7 +2123,8 @@ def _maybe_normalize_endpoints(start, end, normalize):
     return start, end, _normalized
 
 
-def _maybe_localize_point(ts, is_none, is_not_none, freq, tz):
+def _maybe_localize_point(ts, is_none, is_not_none, freq, tz, ambiguous,
+                          nonexistent):
     """
     Localize a start or end Timestamp to the timezone of the corresponding
     start or end Timestamp
@@ -2133,6 +2136,8 @@ def _maybe_localize_point(ts, is_none, is_not_none, freq, tz):
     is_not_none : argument that should not be None
     freq : Tick, DateOffset, or None
     tz : str, timezone object or None
+    ambiguous: str, localization behavior for ambiguous times
+    nonexistent: str, localization behavior for nonexistent times
 
     Returns
     -------
@@ -2141,10 +2146,13 @@ def _maybe_localize_point(ts, is_none, is_not_none, freq, tz):
     # Make sure start and end are timezone localized if:
     # 1) freq = a Timedelta-like frequency (Tick)
     # 2) freq = None i.e. generating a linspaced range
-    if isinstance(freq, Tick) or freq is None:
-        localize_args = {'tz': tz, 'ambiguous': False}
-    else:
-        localize_args = {'tz': None}
     if is_none is None and is_not_none is not None:
+        # Note: We can't ambiguous='infer' a singular ambiguous time; however,
+        # we have historically defaulted ambiguous=False
+        ambiguous = ambiguous if ambiguous != 'infer' else False
+        localize_args = {'ambiguous': ambiguous, 'nonexistent': nonexistent,
+                         'tz': None}
+        if isinstance(freq, Tick) or freq is None:
+            localize_args['tz'] = tz
         ts = ts.tz_localize(**localize_args)
     return ts
diff --git a/pandas/tests/indexes/datetimes/test_timezones.py b/pandas/tests/indexes/datetimes/test_timezones.py
index 908d563eca8fa..088007ba6af4b 100644
--- a/pandas/tests/indexes/datetimes/test_timezones.py
+++ b/pandas/tests/indexes/datetimes/test_timezones.py
@@ -541,12 +541,9 @@ def test_dti_construction_ambiguous_endpoint(self, tz):
         # construction with an ambiguous end-point
         # GH#11626
 
-        # FIXME: This next block fails to raise; it was taken from an older
-        # version of this test that had an indention mistake that caused it
-        # to not get executed.
-        # with pytest.raises(pytz.AmbiguousTimeError):
-        #    date_range("2013-10-26 23:00", "2013-10-27 01:00",
-        #               tz="Europe/London", freq="H")
+        with pytest.raises(pytz.AmbiguousTimeError):
+            date_range("2013-10-26 23:00", "2013-10-27 01:00",
+                       tz="Europe/London", freq="H")
 
         times = date_range("2013-10-26 23:00", "2013-10-27 01:00", freq="H",
                            tz=tz, ambiguous='infer')
@@ -561,6 +558,26 @@ def test_dti_construction_ambiguous_endpoint(self, tz):
             assert times[-1] == Timestamp('2013-10-27 01:00:00+0000',
                                           tz=tz, freq="H")
 
+    @pytest.mark.parametrize('tz, option, expected', [
+        ['US/Pacific', 'shift_forward', "2019-03-10 03:00"],
+        ['dateutil/US/Pacific', 'shift_forward', "2019-03-10 03:00"],
+        ['US/Pacific', 'shift_backward', "2019-03-10 01:00"],
+        pytest.param('dateutil/US/Pacific', 'shift_backward',
+                     "2019-03-10 01:00",
+                     marks=pytest.mark.xfail(reason="GH 24329")),
+        ['US/Pacific', timedelta(hours=1), "2019-03-10 03:00"]
+    ])
+    def test_dti_construction_nonexistent_endpoint(self, tz, option, expected):
+        # construction with an nonexistent end-point
+
+        with pytest.raises(pytz.NonExistentTimeError):
+            date_range("2019-03-10 00:00", "2019-03-10 02:00",
+                       tz="US/Pacific", freq="H")
+
+        times = date_range("2019-03-10 00:00", "2019-03-10 02:00", freq="H",
+                           tz=tz, nonexistent=option)
+        assert times[-1] == Timestamp(expected, tz=tz, freq="H")
+
     def test_dti_tz_localize_bdate_range(self):
         dr = pd.bdate_range('1/1/2009', '1/1/2010')
         dr_utc = pd.bdate_range('1/1/2009', '1/1/2010', tz=pytz.utc)