From 9e5dfedbd26b639d34bc5f32ac1a74851afd758e Mon Sep 17 00:00:00 2001
From: jbrockmendel <jbrockmendel@gmail.com>
Date: Sat, 27 Oct 2018 20:14:13 -0700
Subject: [PATCH] BUG: Fix date_range overflow (#23345)

---
 doc/source/whatsnew/v0.24.0.txt               |  1 +
 pandas/core/arrays/datetimes.py               | 42 ++++++++++++++++++-
 .../indexes/datetimes/test_date_range.py      |  7 ++++
 3 files changed, 48 insertions(+), 2 deletions(-)

diff --git a/doc/source/whatsnew/v0.24.0.txt b/doc/source/whatsnew/v0.24.0.txt
index 70725a347c9d03..b8d63e03e33183 100644
--- a/doc/source/whatsnew/v0.24.0.txt
+++ b/doc/source/whatsnew/v0.24.0.txt
@@ -1027,6 +1027,7 @@ Datetimelike
 - Bug in :class:`PeriodIndex` where adding or subtracting a :class:`timedelta` or :class:`Tick` object produced incorrect results (:issue:`22988`)
 - Bug in :func:`date_range` when decrementing a start date to a past end date by a negative frequency (:issue:`23270`)
 - Bug in :func:`DataFrame.combine` with datetimelike values raising a TypeError (:issue:`23079`)
+- Bug in :func:`date_range` with frequency of ``Day`` or higher where dates sufficiently far in the future could wrap around to the past instead of raising ``OutOfBoundsDatetime`` (:issue:`14187`)
 
 Timedelta
 ^^^^^^^^^
diff --git a/pandas/core/arrays/datetimes.py b/pandas/core/arrays/datetimes.py
index cd20bcbed22118..2392bbdd87f7a3 100644
--- a/pandas/core/arrays/datetimes.py
+++ b/pandas/core/arrays/datetimes.py
@@ -1355,11 +1355,11 @@ def _generate_regular_range(cls, start, end, periods, freq):
             tz = start.tz
         elif start is not None:
             b = Timestamp(start).value
-            e = b + np.int64(periods) * stride
+            e = _generate_range_overflow_safe(b, periods, stride, side='start')
             tz = start.tz
         elif end is not None:
             e = Timestamp(end).value + stride
-            b = e - np.int64(periods) * stride
+            b = _generate_range_overflow_safe(e, periods, stride, side='end')
             tz = end.tz
         else:
             raise ValueError("at least 'start' or 'end' should be specified "
@@ -1384,6 +1384,44 @@ def _generate_regular_range(cls, start, end, periods, freq):
     return data
 
 
+def _generate_range_overflow_safe(endpoint, periods, stride, side='start'):
+    """
+    Calculate the second endpoint for passing to np.arange, checking
+    to avoid an integer overflow.  Catch OverflowError and re-raise
+    as OutOfBoundsDatetime.
+
+    Parameters
+    ----------
+    endpoint : int
+    periods : int
+    stride : int
+    side : {'start', 'end'}
+
+    Returns
+    -------
+    other_end : int
+
+    Raises
+    ------
+    OutOfBoundsDatetime
+    """
+    # GH#14187 raise instead of incorrectly wrapping around
+    assert side in ['start', 'end']
+    if side == 'end':
+        stride *= -1
+
+    try:
+        other_end = checked_add_with_arr(np.int64(endpoint),
+                                         np.int64(periods) * stride)
+    except OverflowError:
+        raise tslib.OutOfBoundsDatetime('Cannot generate range with '
+                                        '{side}={endpoint} and '
+                                        'periods={periods}'
+                                        .format(side=side, endpoint=endpoint,
+                                                periods=periods))
+    return other_end
+
+
 def _infer_tz_from_endpoints(start, end, tz):
     """
     If a timezone is not explicitly given via `tz`, see if one can
diff --git a/pandas/tests/indexes/datetimes/test_date_range.py b/pandas/tests/indexes/datetimes/test_date_range.py
index 657d8ffe0cd389..450d7643bfbd5b 100644
--- a/pandas/tests/indexes/datetimes/test_date_range.py
+++ b/pandas/tests/indexes/datetimes/test_date_range.py
@@ -15,6 +15,7 @@
 from pandas import (
     DatetimeIndex, Timestamp, bdate_range, compat, date_range, offsets
 )
+from pandas.errors import OutOfBoundsDatetime
 from pandas.tests.series.common import TestData
 from pandas.tseries.offsets import (
     BDay, CDay, DateOffset, MonthEnd, generate_range, prefix_mapping
@@ -79,6 +80,12 @@ def test_date_range_timestamp_equiv_preserve_frequency(self):
 
 
 class TestDateRanges(TestData):
+    def test_date_range_out_of_bounds(self):
+        # GH#14187
+        with pytest.raises(OutOfBoundsDatetime):
+            date_range('2016-01-01', periods=100000, freq='D')
+        with pytest.raises(OutOfBoundsDatetime):
+            date_range(end='1763-10-12', periods=100000, freq='D')
 
     def test_date_range_gen_error(self):
         rng = date_range('1/1/2000 00:00', '1/1/2000 00:18', freq='5min')