diff --git a/ravendb/tests/jvm_migrated_tests/client_tests/time_series_tests/test_time_series_ranges_cache.py b/ravendb/tests/jvm_migrated_tests/client_tests/time_series_tests/test_time_series_ranges_cache.py
index 9514f50b..becae6dc 100644
--- a/ravendb/tests/jvm_migrated_tests/client_tests/time_series_tests/test_time_series_ranges_cache.py
+++ b/ravendb/tests/jvm_migrated_tests/client_tests/time_series_tests/test_time_series_ranges_cache.py
@@ -456,3 +456,106 @@ def test_should_merge_time_series_ranges_in_cache_2(self):
 
             self.assertEqual(base_line + timedelta(minutes=0), ranges[0].from_date)
             self.assertEqual(base_line + timedelta(minutes=45), ranges[0].to_date)
+
+    def test_should_merge_time_series_range_in_cache_3(self):
+        base_line = datetime(2023, 8, 20, 21, 30)
+        doc_id = "users/ayende"
+        ts_name = "Heartrate"
+        tag = "watches/fitbit"
+
+        with self.store.open_session() as session:
+            session.store(User(name="Oren"), doc_id)
+            session.save_changes()
+
+        with self.store.open_session() as session:
+            tsf = session.time_series_for(doc_id, ts_name)
+            for i in range(360):
+                tsf.append_single(base_line + timedelta(seconds=i * 10), 60, tag)
+
+            tsf = session.time_series_for(doc_id, ts_name)
+
+            tsf.append_single(base_line + timedelta(hours=1), 70, tag)
+            tsf.append_single(base_line + timedelta(minutes=90), 75, tag)
+
+            session.save_changes()
+
+        with self.store.open_session() as session:
+            vals = session.time_series_for(doc_id, ts_name).get(
+                base_line + timedelta(minutes=1), base_line + timedelta(minutes=2)
+            )
+
+            self.assertEqual(7, len(vals))
+            self.assertEqual(base_line + timedelta(minutes=1), vals[0].timestamp)
+            self.assertEqual(base_line + timedelta(minutes=2), vals[6].timestamp)
+
+            vals = session.time_series_for(doc_id, ts_name).get(
+                base_line + timedelta(minutes=5), base_line + timedelta(minutes=6)
+            )
+
+            self.assertEqual(2, session.advanced.number_of_requests)
+
+            self.assertEqual(7, len(vals))
+            self.assertEqual(base_line + timedelta(minutes=5), vals[0].timestamp)
+            self.assertEqual(base_line + timedelta(minutes=6), vals[6].timestamp)
+
+            cache = session.time_series_by_doc_id.get(doc_id)
+            ranges = cache.get(ts_name)
+            self.assertIsNotNone(ranges)
+            self.assertEqual(2, len(ranges))
+
+            self.assertEqual(base_line + timedelta(minutes=1), ranges[0].from_date)
+            self.assertEqual(base_line + timedelta(minutes=2), ranges[0].to_date)
+            self.assertEqual(base_line + timedelta(minutes=5), ranges[1].from_date)
+            self.assertEqual(base_line + timedelta(minutes=6), ranges[1].to_date)
+
+            # should go to server to get [2, 3] and merge with [1, 2]
+
+            vals = session.time_series_for(doc_id, ts_name).get(
+                base_line + timedelta(minutes=2), base_line + timedelta(minutes=3)
+            )
+            self.assertEqual(3, session.advanced.number_of_requests)
+
+            self.assertEqual(7, len(vals))
+            self.assertEqual(base_line + timedelta(minutes=2), vals[0].timestamp)
+            self.assertEqual(base_line + timedelta(minutes=3), vals[6].timestamp)
+
+            self.assertEqual(2, len(ranges))
+
+            self.assertEqual(base_line + timedelta(minutes=1), ranges[0].from_date)
+            self.assertEqual(base_line + timedelta(minutes=3), ranges[0].to_date)
+            self.assertEqual(base_line + timedelta(minutes=5), ranges[1].from_date)
+            self.assertEqual(base_line + timedelta(minutes=6), ranges[1].to_date)
+
+            # should go to server to get [4, 5] and merge with [5, 6]
+            vals = session.time_series_for(doc_id, ts_name).get(
+                base_line + timedelta(minutes=4), base_line + timedelta(minutes=5)
+            )
+            self.assertEqual(4, session.advanced.number_of_requests)
+
+            self.assertEqual(7, len(vals))
+            self.assertEqual(base_line + timedelta(minutes=4), vals[0].timestamp)
+            self.assertEqual(base_line + timedelta(minutes=5), vals[6].timestamp)
+
+            self.assertEqual(2, len(ranges))
+
+            self.assertEqual(base_line + timedelta(minutes=1), ranges[0].from_date)
+            self.assertEqual(base_line + timedelta(minutes=3), ranges[0].to_date)
+            self.assertEqual(base_line + timedelta(minutes=4), ranges[1].from_date)
+            self.assertEqual(base_line + timedelta(minutes=6), ranges[1].to_date)
+
+            # should go to server to get [3, 4] and merge all ranges into [1, 6]
+
+            vals = session.time_series_for(doc_id, ts_name).get(
+                base_line + timedelta(minutes=3), base_line + timedelta(minutes=4)
+            )
+
+            self.assertEqual(5, session.advanced.number_of_requests)
+
+            self.assertEqual(7, len(vals))
+            self.assertEqual(base_line + timedelta(minutes=3), vals[0].timestamp)
+            self.assertEqual(base_line + timedelta(minutes=4), vals[6].timestamp)
+
+            self.assertEqual(1, len(ranges))
+
+            self.assertEqual(base_line + timedelta(minutes=1), ranges[0].from_date)
+            self.assertEqual(base_line + timedelta(minutes=6), ranges[0].to_date)