diff --git a/ravendb/tests/jvm_migrated_tests/client_tests/time_series_tests/test_time_series_operations.py b/ravendb/tests/jvm_migrated_tests/client_tests/time_series_tests/test_time_series_operations.py
index 179fcfbd..693a720e 100644
--- a/ravendb/tests/jvm_migrated_tests/client_tests/time_series_tests/test_time_series_operations.py
+++ b/ravendb/tests/jvm_migrated_tests/client_tests/time_series_tests/test_time_series_operations.py
@@ -1,5 +1,6 @@
 from datetime import datetime, timedelta
 
+from ravendb import SessionOptions
 from ravendb.documents.operations.time_series import (
     GetTimeSeriesOperation,
     TimeSeriesOperation,
@@ -9,6 +10,7 @@
     TimeSeriesDetails,
 )
 from ravendb.documents.session.time_series import TimeSeriesRange
+from ravendb.tests.jvm_migrated_tests.client_tests.time_series_tests.test_time_series_raw_query import RawQueryResult
 from ravendb.tests.test_base import TestBase, User
 
 
@@ -464,3 +466,99 @@ def test_get_time_series_should_throw_on_missing_name(self):
             self.assertIn(ex.args[0], "Timeseries cannot be None or empty")
 
         self.assertTrue(failed)
+
+    def test_can_delete_large_range(self):
+        document_id = "foo/bar"
+        base_line = datetime(2023, 8, 20, 0, 0) - timedelta(seconds=1)
+
+        with self.store.open_session() as session:
+            session.store(User(), document_id)
+            tsf = session.time_series_for(document_id, "BloodPressure")
+
+            for j in range(1, 10000, 1):
+                offset = j * 10
+                time = base_line + timedelta(seconds=offset)
+
+                tsf.append(time, [j], "watches/apple")
+
+            session.save_changes()
+
+        raw_query = (
+            "declare timeseries blood_pressure(doc)\n"
+            "  {\n"
+            "      from doc.BloodPressure between $start and $end\n"
+            "      group by 1h\n"
+            "      select min(), max(), avg(), first(), last()\n"
+            "  }\n"
+            "  from Users as p\n"
+            "  select blood_pressure(p) as blood_pressure"
+        )
+
+        with self.store.open_session() as session:
+            query = (
+                session.advanced.raw_query(raw_query, RawQueryResult)
+                .add_parameter("start", base_line)
+                .add_parameter("end", base_line + timedelta(days=1))
+            )
+
+            result = list(query)
+
+            self.assertEqual(1, len(result))
+
+            agg = result[0]
+
+            blood_pressure = agg.blood_pressure
+            count = sum(map(lambda x: x.count[0], blood_pressure.results))
+            self.assertEqual(8640, count)
+            self.assertEqual(blood_pressure.count, count)
+            self.assertEqual(24, len(blood_pressure.results))
+
+            for index in range(len(blood_pressure.results)):
+                item = blood_pressure.results[index]
+                self.assertEqual(360, item.count[0])
+                self.assertEqual(index * 360 + 180 + 0.5, item.average[0])
+                self.assertEqual((index + 1) * 360, item.max[0])
+                self.assertEqual(index * 360 + 1, item.min[0])
+                self.assertEqual(index * 360 + 1, item.first[0])
+                self.assertEqual((index + 1) * 360, item.last[0])
+
+        with self.store.open_session() as session:
+            tsf = session.time_series_for(document_id, "BloodPressure")
+            tsf.delete(base_line + timedelta(seconds=3600), base_line + timedelta(seconds=3600 * 10))  # remove 9 hours
+            session.save_changes()
+
+        session_options = SessionOptions(no_caching=True)
+        with self.store.open_session(session_options=session_options) as session:
+            query = (
+                session.advanced.raw_query(raw_query, RawQueryResult)
+                .add_parameter("start", base_line)
+                .add_parameter("end", base_line + timedelta(days=1))
+            )
+            result = list(query)
+            agg = result[0]
+            blood_pressure = agg.blood_pressure
+            count = sum(map(lambda x: x.count[0], blood_pressure.results))
+            self.assertEqual(5399, count)
+            self.assertEqual(blood_pressure.count, count)
+            self.assertEqual(15, len(blood_pressure.results))
+
+            index = 0
+
+            item = blood_pressure.results[index]
+            self.assertEqual(359, item.count[0])
+            self.assertEqual(180, item.average[0])
+            self.assertEqual(359, item.max[0])
+            self.assertEqual(1, item.min[0])
+            self.assertEqual(1, item.first[0])
+            self.assertEqual(359, item.last[0])
+
+            for index in range(1, len(blood_pressure.results)):
+                item = blood_pressure.results[index]
+                real_index = index + 9
+
+                self.assertEqual(360, item.count[0])
+                self.assertEqual(real_index * 360 + 180 + 0.5, item.average[0])
+                self.assertEqual((real_index + 1) * 360, item.max[0])
+                self.assertEqual(real_index * 360 + 1, item.min[0])
+                self.assertEqual(real_index * 360 + 1, item.first[0])
+                self.assertEqual((real_index + 1) * 360, item.last[0])