diff --git a/synapse/storage/__init__.py b/synapse/storage/__init__.py
index 0099a3f5bb..9996f195a0 100644
--- a/synapse/storage/__init__.py
+++ b/synapse/storage/__init__.py
@@ -222,6 +222,8 @@ class DataStore(RoomMemberStore, RoomStore,
             self._find_stream_orderings_for_times, 60 * 60 * 1000
         )
 
+        self._stream_order_on_start = self.get_room_max_stream_ordering()
+
         super(DataStore, self).__init__(hs)
 
     def take_presence_startup_info(self):
diff --git a/synapse/storage/event_federation.py b/synapse/storage/event_federation.py
index 59b4cf1e53..765b5a5bcb 100644
--- a/synapse/storage/event_federation.py
+++ b/synapse/storage/event_federation.py
@@ -348,7 +348,14 @@ class EventFederationStore(SQLBaseStore):
         # We want to make the cache more effective, so we clamp to the last
         # change before the given ordering.
         last_change = self._events_stream_cache.get_max_pos_of_last_change(room_id)
-        stream_ordering = min(last_change, stream_ordering)
+
+        # We don't always have a full stream_to_exterm_id table, e.g. after
+        # the upgrade that introduced it, so we make sure we never ask for a
+        # try and pin to a stream_ordering from before a restart
+        last_change = max(self._stream_order_on_start, last_change)
+
+        if last_change > self.stream_ordering_month_ago:
+            stream_ordering = min(last_change, stream_ordering)
 
         return self._get_forward_extremeties_for_room(room_id, stream_ordering)
 
@@ -386,9 +393,19 @@ class EventFederationStore(SQLBaseStore):
 
     def _delete_old_forward_extrem_cache(self):
         def _delete_old_forward_extrem_cache_txn(txn):
+            sql = ("""
+                DELETE FROM stream_ordering_to_exterm
+                WHERE
+                (
+                    SELECT max(stream_ordering) AS stream_ordering
+                    FROM stream_ordering_to_exterm
+                    WHERE room_id = stream_ordering_to_exterm.room_id
+                ) > ?
+                AND stream_ordering < ?
+            """)
             txn.execute(
-                "DELETE FROM stream_ordering_to_exterm WHERE stream_ordering < ?",
-                (self.stream_ordering_month_ago,)
+                sql,
+                (self.stream_ordering_month_ago, self.stream_ordering_month_ago,)
             )
         return self.runInteraction(
             "_delete_old_forward_extrem_cache",