diff --git a/tests/federation/test_federation_catch_up.py b/tests/federation/test_federation_catch_up.py
index cc52c3dfac..1a3ccb263d 100644
--- a/tests/federation/test_federation_catch_up.py
+++ b/tests/federation/test_federation_catch_up.py
@@ -321,3 +321,102 @@ class FederationCatchUpTestCases(FederatingHomeserverTestCase):
per_dest_queue._last_successful_stream_ordering,
event_5.internal_metadata.stream_ordering,
)
+
+ @override_config({"send_federation": True})
+ def test_catch_up_on_synapse_startup(self):
+ """
+ Tests the behaviour of get_catch_up_outstanding_destinations and
+ _wake_destinations_needing_catchup.
+ """
+
+ # list of sorted server names (note that there are more servers than the batch
+ # size used in get_catch_up_outstanding_destinations).
+ server_names = ["server%02d" % number for number in range(42)] + ["zzzerver"]
+
+ # ARRANGE:
+ # - a local user (u1)
+ # - a room which u1 is joined to (and remote users @user:serverXX are
+ # joined to)
+
+ # mark the remotes as online
+ self.is_online = True
+
+ self.register_user("u1", "you the one")
+ u1_token = self.login("u1", "you the one")
+ room_id = self.helper.create_room_as("u1", tok=u1_token)
+
+ for server_name in server_names:
+ self.get_success(
+ event_injection.inject_member_event(
+ self.hs, room_id, "@user:%s" % server_name, "join"
+ )
+ )
+
+ # create an event
+ self.helper.send(room_id, "deary me!", tok=u1_token)
+
+ # ASSERT:
+ # - All servers are up to date so none should have outstanding catch-up
+ outstanding_when_successful = self.get_success(
+ self.hs.get_datastore().get_catch_up_outstanding_destinations(None)
+ )
+ self.assertEqual(outstanding_when_successful, [])
+
+ # ACT:
+ # - Make the remote servers unreachable
+ self.is_online = False
+
+ # - Mark zzzerver as being backed-off from
+ now = self.clock.time_msec()
+ self.get_success(
+ self.hs.get_datastore().set_destination_retry_timings(
+ "zzzerver", now, now, 24 * 60 * 60 * 1000 # retry in 1 day
+ )
+ )
+
+ # - Send an event
+ self.helper.send(room_id, "can anyone hear me?", tok=u1_token)
+
+ # ASSERT (get_catch_up_outstanding_destinations):
+ # - all remotes are outstanding
+ # - they are returned in batches of 25, in order
+ outstanding_1 = self.get_success(
+ self.hs.get_datastore().get_catch_up_outstanding_destinations(None)
+ )
+
+ self.assertEqual(len(outstanding_1), 25)
+ self.assertEqual(outstanding_1, server_names[0:25])
+
+ outstanding_2 = self.get_success(
+ self.hs.get_datastore().get_catch_up_outstanding_destinations(
+ outstanding_1[-1]
+ )
+ )
+ self.assertNotIn("zzzerver", outstanding_2)
+ self.assertEqual(len(outstanding_2), 17)
+ self.assertEqual(outstanding_2, server_names[25:-1])
+
+ # ACT: call _wake_destinations_needing_catchup
+
+ # patch wake_destination to just count the destinations instead
+ woken = []
+
+ def wake_destination_track(destination):
+ woken.append(destination)
+
+ self.hs.get_federation_sender().wake_destination = wake_destination_track
+
+ # cancel the pre-existing timer for _wake_destinations_needing_catchup
+ # this is because we are calling it manually rather than waiting for it
+ # to be called automatically
+ self.hs.get_federation_sender()._catchup_after_startup_timer.cancel()
+
+ self.get_success(
+ self.hs.get_federation_sender()._wake_destinations_needing_catchup(), by=5.0
+ )
+
+ # ASSERT (_wake_destinations_needing_catchup):
+ # - all remotes are woken up, save for zzzerver
+ self.assertNotIn("zzzerver", woken)
+ # - all destinations are woken exactly once; they appear once in woken.
+ self.assertCountEqual(woken, server_names[:-1])
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