diff --git a/synapse/handlers/message.py b/synapse/handlers/message.py
index 32548e66f..3d7f97bcf 100644
--- a/synapse/handlers/message.py
+++ b/synapse/handlers/message.py
@@ -277,10 +277,13 @@ class MessageHandler(BaseRoomHandler):
                     end_token=now_token.events_key,
                 )
 
+                start_token = now_token.copy_and_replace("events_key", token[0])
+                end_token = now_token.copy_and_replace("events_key", token[1])
+
                 d["messages"] = {
                     "chunk": [m.get_dict() for m in messages],
-                    "start": token[0],
-                    "end": token[1],
+                    "start": start_token.to_string(),
+                    "end": end_token.to_string(),
                 }
 
                 current_state = yield self.store.get_current_state(
diff --git a/synapse/storage/stream.py b/synapse/storage/stream.py
index 4945b0796..0b7822282 100644
--- a/synapse/storage/stream.py
+++ b/synapse/storage/stream.py
@@ -205,8 +205,11 @@ class StreamStore(SQLBaseStore):
                              with_feedback=False):
         # TODO (erikj): Handle compressed feedback
 
-        from_comp = '<' if direction =='b' else '>'
-        to_comp = '>' if direction =='b' else '<'
+        # Tokens really represent positions between elements, but we use
+        # the convention of pointing to the event before the gap. Hence
+        # we have a bit of asymmetry when it comes to equalities.
+        from_comp = '<=' if direction =='b' else '>'
+        to_comp = '>' if direction =='b' else '<='
         order = "DESC" if direction == 'b' else "ASC"
 
         args = [room_id]