diff --git a/changelog.d/17688.misc b/changelog.d/17688.misc
new file mode 100644
index 0000000000..7ba8d48fbe
--- /dev/null
+++ b/changelog.d/17688.misc
@@ -0,0 +1 @@
+Speed up sync by pulling out fewer events from the database.
diff --git a/synapse/handlers/admin.py b/synapse/handlers/admin.py
index c874d22eac..65b3f153da 100644
--- a/synapse/handlers/admin.py
+++ b/synapse/handlers/admin.py
@@ -200,6 +200,7 @@ async def export_user_data(self, user_id: str, writer: "ExfiltrationWriter") ->
                 (
                     events,
                     _,
+                    _,
                 ) = await self._store.paginate_room_events_by_topological_ordering(
                     room_id=room_id,
                     from_key=from_key,
diff --git a/synapse/handlers/pagination.py b/synapse/handlers/pagination.py
index 3c44458fa3..4070b74b7a 100644
--- a/synapse/handlers/pagination.py
+++ b/synapse/handlers/pagination.py
@@ -510,6 +510,7 @@ async def get_messages(
         (
             events,
             next_key,
+            _,
         ) = await self.store.paginate_room_events_by_topological_ordering(
             room_id=room_id,
             from_key=from_token.room_key,
@@ -588,6 +589,7 @@ async def get_messages(
                     (
                         events,
                         next_key,
+                        _,
                     ) = await self.store.paginate_room_events_by_topological_ordering(
                         room_id=room_id,
                         from_key=from_token.room_key,
diff --git a/synapse/handlers/room.py b/synapse/handlers/room.py
index 35c88f1b91..386375d64b 100644
--- a/synapse/handlers/room.py
+++ b/synapse/handlers/room.py
@@ -1753,7 +1753,7 @@ async def get_new_events(
             )
 
             events = list(room_events)
-            events.extend(e for evs, _ in room_to_events.values() for e in evs)
+            events.extend(e for evs, _, _ in room_to_events.values() for e in evs)
 
             # We know stream_ordering must be not None here, as its been
             # persisted, but mypy doesn't know that
diff --git a/synapse/handlers/sliding_sync/__init__.py b/synapse/handlers/sliding_sync/__init__.py
index 7340c6ec05..cf368be9d9 100644
--- a/synapse/handlers/sliding_sync/__init__.py
+++ b/synapse/handlers/sliding_sync/__init__.py
@@ -47,7 +47,6 @@
     MutableStateMap,
     PersistedEventPosition,
     Requester,
-    RoomStreamToken,
     SlidingSyncStreamToken,
     StateMap,
     StreamKeyType,
@@ -632,7 +631,7 @@ async def get_room_sync_data(
                 # Use `stream_ordering` for updates
                 else paginate_room_events_by_stream_ordering
             )
-            timeline_events, new_room_key = await pagination_method(
+            timeline_events, new_room_key, limited = await pagination_method(
                 room_id=room_id,
                 # The bounds are reversed so we can paginate backwards
                 # (from newer to older events) starting at to_bound.
@@ -640,28 +639,13 @@ async def get_room_sync_data(
                 from_key=to_bound,
                 to_key=timeline_from_bound,
                 direction=Direction.BACKWARDS,
-                # We add one so we can determine if there are enough events to saturate
-                # the limit or not (see `limited`)
-                limit=room_sync_config.timeline_limit + 1,
+                limit=room_sync_config.timeline_limit,
             )
 
             # We want to return the events in ascending order (the last event is the
             # most recent).
             timeline_events.reverse()
 
-            # Determine our `limited` status based on the timeline. We do this before
-            # filtering the events so we can accurately determine if there is more to
-            # paginate even if we filter out some/all events.
-            if len(timeline_events) > room_sync_config.timeline_limit:
-                limited = True
-                # Get rid of that extra "+ 1" event because we only used it to determine
-                # if we hit the limit or not
-                timeline_events = timeline_events[-room_sync_config.timeline_limit :]
-                assert timeline_events[0].internal_metadata.stream_ordering
-                new_room_key = RoomStreamToken(
-                    stream=timeline_events[0].internal_metadata.stream_ordering - 1
-                )
-
             # Make sure we don't expose any events that the client shouldn't see
             timeline_events = await filter_events_for_client(
                 self.storage_controllers,
diff --git a/synapse/handlers/sync.py b/synapse/handlers/sync.py
index 609840bfe9..f4ea90fbd7 100644
--- a/synapse/handlers/sync.py
+++ b/synapse/handlers/sync.py
@@ -906,7 +906,7 @@ async def _load_filtered_recents(
                     # Use `stream_ordering` for updates
                     else paginate_room_events_by_stream_ordering
                 )
-                events, end_key = await pagination_method(
+                events, end_key, limited = await pagination_method(
                     room_id=room_id,
                     # The bounds are reversed so we can paginate backwards
                     # (from newer to older events) starting at to_bound.
@@ -914,9 +914,7 @@ async def _load_filtered_recents(
                     from_key=end_key,
                     to_key=since_key,
                     direction=Direction.BACKWARDS,
-                    # We add one so we can determine if there are enough events to saturate
-                    # the limit or not (see `limited`)
-                    limit=load_limit + 1,
+                    limit=load_limit,
                 )
                 # We want to return the events in ascending order (the last event is the
                 # most recent).
@@ -971,9 +969,6 @@ async def _load_filtered_recents(
                 loaded_recents.extend(recents)
                 recents = loaded_recents
 
-                if len(events) <= load_limit:
-                    limited = False
-                    break
                 max_repeat -= 1
 
             if len(recents) > timeline_limit:
@@ -2608,7 +2603,7 @@ async def _get_room_changes_for_incremental_sync(
 
             newly_joined = room_id in newly_joined_rooms
             if room_entry:
-                events, start_key = room_entry
+                events, start_key, _ = room_entry
                 # We want to return the events in ascending order (the last event is the
                 # most recent).
                 events.reverse()
diff --git a/synapse/storage/databases/main/stream.py b/synapse/storage/databases/main/stream.py
index 68d4168621..459436e304 100644
--- a/synapse/storage/databases/main/stream.py
+++ b/synapse/storage/databases/main/stream.py
@@ -108,7 +108,7 @@ async def __call__(
         to_key: Optional[RoomStreamToken] = None,
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
-    ) -> Tuple[List[EventBase], RoomStreamToken]: ...
+    ) -> Tuple[List[EventBase], RoomStreamToken, bool]: ...
 
 
 # Used as return values for pagination APIs
@@ -679,7 +679,7 @@ async def get_room_events_stream_for_rooms(
         to_key: Optional[RoomStreamToken] = None,
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
-    ) -> Dict[str, Tuple[List[EventBase], RoomStreamToken]]:
+    ) -> Dict[str, Tuple[List[EventBase], RoomStreamToken, bool]]:
         """Get new room events in stream ordering since `from_key`.
 
         Args:
@@ -695,6 +695,7 @@ async def get_room_events_stream_for_rooms(
             A map from room id to a tuple containing:
                 - list of recent events in the room
                 - stream ordering key for the start of the chunk of events returned.
+                - a boolean to indicate if there were more events but we hit the limit
 
             When Direction.FORWARDS: from_key < x <= to_key, (ascending order)
             When Direction.BACKWARDS: from_key >= x > to_key, (descending order)
@@ -758,7 +759,7 @@ async def paginate_room_events_by_stream_ordering(
         to_key: Optional[RoomStreamToken] = None,
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
-    ) -> Tuple[List[EventBase], RoomStreamToken]:
+    ) -> Tuple[List[EventBase], RoomStreamToken, bool]:
         """
         Paginate events by `stream_ordering` in the room from the `from_key` in the
         given `direction` to the `to_key` or `limit`.
@@ -773,8 +774,9 @@ async def paginate_room_events_by_stream_ordering(
             limit: Maximum number of events to return
 
         Returns:
-            The results as a list of events and a token that points to the end
-            of the result set. If no events are returned then the end of the
+            The results as a list of events, a token that points to the end of
+            the result set, and a boolean to indicate if there were more events
+            but we hit the limit. If no events are returned then the end of the
             stream has been reached (i.e. there are no events between `from_key`
             and `to_key`).
 
@@ -798,7 +800,7 @@ async def paginate_room_events_by_stream_ordering(
             and to_key.is_before_or_eq(from_key)
         ):
             # Token selection matches what we do below if there are no rows
-            return [], to_key if to_key else from_key
+            return [], to_key if to_key else from_key, False
         # Or vice-versa, if we're looking backwards and our `from_key` is already before
         # our `to_key`.
         elif (
@@ -807,7 +809,7 @@ async def paginate_room_events_by_stream_ordering(
             and from_key.is_before_or_eq(to_key)
         ):
             # Token selection matches what we do below if there are no rows
-            return [], to_key if to_key else from_key
+            return [], to_key if to_key else from_key, False
 
         # We can do a quick sanity check to see if any events have been sent in the room
         # since the earlier token.
@@ -826,7 +828,7 @@ async def paginate_room_events_by_stream_ordering(
 
         if not has_changed:
             # Token selection matches what we do below if there are no rows
-            return [], to_key if to_key else from_key
+            return [], to_key if to_key else from_key, False
 
         order, from_bound, to_bound = generate_pagination_bounds(
             direction, from_key, to_key
@@ -842,7 +844,7 @@ async def paginate_room_events_by_stream_ordering(
             engine=self.database_engine,
         )
 
-        def f(txn: LoggingTransaction) -> List[_EventDictReturn]:
+        def f(txn: LoggingTransaction) -> Tuple[List[_EventDictReturn], bool]:
             sql = f"""
                 SELECT event_id, instance_name, stream_ordering
                 FROM events
@@ -854,9 +856,13 @@ def f(txn: LoggingTransaction) -> List[_EventDictReturn]:
             """
             txn.execute(sql, (room_id, 2 * limit))
 
+            # Get all the rows and check if we hit the limit.
+            fetched_rows = txn.fetchall()
+            limited = len(fetched_rows) >= 2 * limit
+
             rows = [
                 _EventDictReturn(event_id, None, stream_ordering)
-                for event_id, instance_name, stream_ordering in txn
+                for event_id, instance_name, stream_ordering in fetched_rows
                 if _filter_results_by_stream(
                     lower_token=(
                         to_key if direction == Direction.BACKWARDS else from_key
@@ -867,10 +873,17 @@ def f(txn: LoggingTransaction) -> List[_EventDictReturn]:
                     instance_name=instance_name,
                     stream_ordering=stream_ordering,
                 )
-            ][:limit]
-            return rows
+            ]
+
+            if len(rows) > limit:
+                limited = True
 
-        rows = await self.db_pool.runInteraction("get_room_events_stream_for_room", f)
+            rows = rows[:limit]
+            return rows, limited
+
+        rows, limited = await self.db_pool.runInteraction(
+            "get_room_events_stream_for_room", f
+        )
 
         ret = await self.get_events_as_list(
             [r.event_id for r in rows], get_prev_content=True
@@ -887,7 +900,7 @@ def f(txn: LoggingTransaction) -> List[_EventDictReturn]:
             # `_paginate_room_events_by_topological_ordering_txn(...)`)
             next_key = to_key if to_key else from_key
 
-        return ret, next_key
+        return ret, next_key, limited
 
     @trace
     async def get_current_state_delta_membership_changes_for_user(
@@ -1191,7 +1204,7 @@ async def get_recent_event_ids_for_room(
         if limit == 0:
             return [], end_token
 
-        rows, token = await self.db_pool.runInteraction(
+        rows, token, _ = await self.db_pool.runInteraction(
             "get_recent_event_ids_for_room",
             self._paginate_room_events_by_topological_ordering_txn,
             room_id,
@@ -1765,7 +1778,7 @@ def _get_events_around_txn(
             topological=topological_ordering, stream=stream_ordering
         )
 
-        rows, start_token = self._paginate_room_events_by_topological_ordering_txn(
+        rows, start_token, _ = self._paginate_room_events_by_topological_ordering_txn(
             txn,
             room_id,
             before_token,
@@ -1775,7 +1788,7 @@ def _get_events_around_txn(
         )
         events_before = [r.event_id for r in rows]
 
-        rows, end_token = self._paginate_room_events_by_topological_ordering_txn(
+        rows, end_token, _ = self._paginate_room_events_by_topological_ordering_txn(
             txn,
             room_id,
             after_token,
@@ -1947,7 +1960,7 @@ def _paginate_room_events_by_topological_ordering_txn(
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
         event_filter: Optional[Filter] = None,
-    ) -> Tuple[List[_EventDictReturn], RoomStreamToken]:
+    ) -> Tuple[List[_EventDictReturn], RoomStreamToken, bool]:
         """Returns list of events before or after a given token.
 
         Args:
@@ -1962,10 +1975,11 @@ def _paginate_room_events_by_topological_ordering_txn(
                 those that match the filter.
 
         Returns:
-            A list of _EventDictReturn and a token that points to the end of the
-            result set. If no events are returned then the end of the stream has
-            been reached (i.e. there are no events between `from_token` and
-            `to_token`), or `limit` is zero.
+            A list of _EventDictReturn, a token that points to the end of the
+            result set, and a boolean to indicate if there were more events but
+            we hit the limit.  If no events are returned then the end of the
+            stream has been reached (i.e. there are no events between
+            `from_token` and `to_token`), or `limit` is zero.
         """
         # We can bail early if we're looking forwards, and our `to_key` is already
         # before our `from_token`.
@@ -1975,7 +1989,7 @@ def _paginate_room_events_by_topological_ordering_txn(
             and to_token.is_before_or_eq(from_token)
         ):
             # Token selection matches what we do below if there are no rows
-            return [], to_token if to_token else from_token
+            return [], to_token if to_token else from_token, False
         # Or vice-versa, if we're looking backwards and our `from_token` is already before
         # our `to_token`.
         elif (
@@ -1984,7 +1998,7 @@ def _paginate_room_events_by_topological_ordering_txn(
             and from_token.is_before_or_eq(to_token)
         ):
             # Token selection matches what we do below if there are no rows
-            return [], to_token if to_token else from_token
+            return [], to_token if to_token else from_token, False
 
         args: List[Any] = [room_id]
 
@@ -2007,6 +2021,7 @@ def _paginate_room_events_by_topological_ordering_txn(
             args.extend(filter_args)
 
         # We fetch more events as we'll filter the result set
+        requested_limit = int(limit) * 2
         args.append(int(limit) * 2)
 
         select_keywords = "SELECT"
@@ -2071,10 +2086,14 @@ def _paginate_room_events_by_topological_ordering_txn(
         }
         txn.execute(sql, args)
 
+        # Get all the rows and check if we hit the limit.
+        fetched_rows = txn.fetchall()
+        limited = len(fetched_rows) >= requested_limit
+
         # Filter the result set.
         rows = [
             _EventDictReturn(event_id, topological_ordering, stream_ordering)
-            for event_id, instance_name, topological_ordering, stream_ordering in txn
+            for event_id, instance_name, topological_ordering, stream_ordering in fetched_rows
             if _filter_results(
                 lower_token=(
                     to_token if direction == Direction.BACKWARDS else from_token
@@ -2086,7 +2105,12 @@ def _paginate_room_events_by_topological_ordering_txn(
                 topological_ordering=topological_ordering,
                 stream_ordering=stream_ordering,
             )
-        ][:limit]
+        ]
+
+        if len(rows) > limit:
+            limited = True
+
+        rows = rows[:limit]
 
         if rows:
             assert rows[-1].topological_ordering is not None
@@ -2097,7 +2121,7 @@ def _paginate_room_events_by_topological_ordering_txn(
             # TODO (erikj): We should work out what to do here instead.
             next_token = to_token if to_token else from_token
 
-        return rows, next_token
+        return rows, next_token, limited
 
     @trace
     @tag_args
@@ -2110,7 +2134,7 @@ async def paginate_room_events_by_topological_ordering(
         direction: Direction = Direction.BACKWARDS,
         limit: int = 0,
         event_filter: Optional[Filter] = None,
-    ) -> Tuple[List[EventBase], RoomStreamToken]:
+    ) -> Tuple[List[EventBase], RoomStreamToken, bool]:
         """
         Paginate events by `topological_ordering` (tie-break with `stream_ordering`) in
         the room from the `from_key` in the given `direction` to the `to_key` or
@@ -2127,8 +2151,9 @@ async def paginate_room_events_by_topological_ordering(
             event_filter: If provided filters the events to those that match the filter.
 
         Returns:
-            The results as a list of events and a token that points to the end
-            of the result set. If no events are returned then the end of the
+            The results as a list of events, a token that points to the end of
+            the result set, and a boolean to indicate if there were more events
+            but we hit the limit. If no events are returned then the end of the
             stream has been reached (i.e. there are no events between `from_key`
             and `to_key`).
 
@@ -2152,7 +2177,7 @@ async def paginate_room_events_by_topological_ordering(
         ):
             # Token selection matches what we do in `_paginate_room_events_txn` if there
             # are no rows
-            return [], to_key if to_key else from_key
+            return [], to_key if to_key else from_key, False
         # Or vice-versa, if we're looking backwards and our `from_key` is already before
         # our `to_key`.
         elif (
@@ -2162,9 +2187,9 @@ async def paginate_room_events_by_topological_ordering(
         ):
             # Token selection matches what we do in `_paginate_room_events_txn` if there
             # are no rows
-            return [], to_key if to_key else from_key
+            return [], to_key if to_key else from_key, False
 
-        rows, token = await self.db_pool.runInteraction(
+        rows, token, limited = await self.db_pool.runInteraction(
             "paginate_room_events_by_topological_ordering",
             self._paginate_room_events_by_topological_ordering_txn,
             room_id,
@@ -2179,7 +2204,7 @@ async def paginate_room_events_by_topological_ordering(
             [r.event_id for r in rows], get_prev_content=True
         )
 
-        return events, token
+        return events, token, limited
 
     @cached()
     async def get_id_for_instance(self, instance_name: str) -> int:
diff --git a/tests/rest/client/sliding_sync/test_rooms_timeline.py b/tests/rest/client/sliding_sync/test_rooms_timeline.py
index 0e027ff39d..2293994793 100644
--- a/tests/rest/client/sliding_sync/test_rooms_timeline.py
+++ b/tests/rest/client/sliding_sync/test_rooms_timeline.py
@@ -22,7 +22,7 @@
 from synapse.api.constants import EventTypes
 from synapse.rest.client import login, room, sync
 from synapse.server import HomeServer
-from synapse.types import StreamToken, StrSequence
+from synapse.types import StrSequence
 from synapse.util import Clock
 
 from tests.rest.client.sliding_sync.test_sliding_sync import SlidingSyncBase
@@ -149,16 +149,10 @@ def test_rooms_limited_initial_sync(self) -> None:
         user2_tok = self.login(user2_id, "pass")
 
         room_id1 = self.helper.create_room_as(user2_id, tok=user2_tok)
-        self.helper.send(room_id1, "activity1", tok=user2_tok)
-        self.helper.send(room_id1, "activity2", tok=user2_tok)
+        event_response1 = self.helper.send(room_id1, "activity1", tok=user2_tok)
+        event_response2 = self.helper.send(room_id1, "activity2", tok=user2_tok)
         event_response3 = self.helper.send(room_id1, "activity3", tok=user2_tok)
-        event_pos3 = self.get_success(
-            self.store.get_position_for_event(event_response3["event_id"])
-        )
         event_response4 = self.helper.send(room_id1, "activity4", tok=user2_tok)
-        event_pos4 = self.get_success(
-            self.store.get_position_for_event(event_response4["event_id"])
-        )
         event_response5 = self.helper.send(room_id1, "activity5", tok=user2_tok)
         user1_join_response = self.helper.join(room_id1, user1_id, tok=user1_tok)
 
@@ -196,27 +190,23 @@ def test_rooms_limited_initial_sync(self) -> None:
         )
 
         # Check to make sure the `prev_batch` points at the right place
-        prev_batch_token = self.get_success(
-            StreamToken.from_string(
-                self.store, response_body["rooms"][room_id1]["prev_batch"]
-            )
-        )
-        prev_batch_room_stream_token_serialized = self.get_success(
-            prev_batch_token.room_key.to_string(self.store)
-        )
-        # If we use the `prev_batch` token to look backwards, we should see `event3`
-        # next so make sure the token encompasses it
-        self.assertEqual(
-            event_pos3.persisted_after(prev_batch_token.room_key),
-            False,
-            f"`prev_batch` token {prev_batch_room_stream_token_serialized} should be >= event_pos3={self.get_success(event_pos3.to_room_stream_token().to_string(self.store))}",
-        )
-        # If we use the `prev_batch` token to look backwards, we shouldn't see `event4`
-        # anymore since it was just returned in this response.
-        self.assertEqual(
-            event_pos4.persisted_after(prev_batch_token.room_key),
-            True,
-            f"`prev_batch` token {prev_batch_room_stream_token_serialized} should be < event_pos4={self.get_success(event_pos4.to_room_stream_token().to_string(self.store))}",
+        prev_batch_token = response_body["rooms"][room_id1]["prev_batch"]
+
+        # If we use the `prev_batch` token to look backwards we should see
+        # `event3` and older next.
+        channel = self.make_request(
+            "GET",
+            f"/rooms/{room_id1}/messages?from={prev_batch_token}&dir=b&limit=3",
+            access_token=user1_tok,
+        )
+        self.assertEqual(channel.code, 200, channel.json_body)
+        self.assertListEqual(
+            [
+                event_response3["event_id"],
+                event_response2["event_id"],
+                event_response1["event_id"],
+            ],
+            [ev["event_id"] for ev in channel.json_body["chunk"]],
         )
 
         # With no `from_token` (initial sync), it's all historical since there is no
diff --git a/tests/storage/test_stream.py b/tests/storage/test_stream.py
index 7b7590da76..837eb434aa 100644
--- a/tests/storage/test_stream.py
+++ b/tests/storage/test_stream.py
@@ -147,7 +147,7 @@ def prepare(
     def _filter_messages(self, filter: JsonDict) -> List[str]:
         """Make a request to /messages with a filter, returns the chunk of events."""
 
-        events, next_key = self.get_success(
+        events, next_key, _ = self.get_success(
             self.hs.get_datastores().main.paginate_room_events_by_topological_ordering(
                 room_id=self.room_id,
                 from_key=self.from_token.room_key,