diff --git a/tests/10apidoc/01register.pl b/tests/10apidoc/01register.pl
index 91866ef16..7114ba06f 100644
--- a/tests/10apidoc/01register.pl
+++ b/tests/10apidoc/01register.pl
@@ -442,6 +442,25 @@ sub remote_user_fixture
    );
 }
 
+push @EXPORT, qw( remote_admin_fixture );
+
+sub remote_admin_fixture
+{
+   my %args = @_;
+
+   fixture(
+      name => "remote_admin_fixture",
+
+      requires => [ $main::API_CLIENTS[1], localpart_fixture(), qw( can_register_with_secret ) ],
+
+      setup => sub {
+         my ( $http, $localpart ) = @_;
+
+         matrix_admin_register_user_via_secret( $http, $localpart, is_admin => 1, %args );
+      }
+   );
+}
+
 sub setup_user
 {
    my ( $http, $localpart, %args ) = @_;
diff --git a/tests/53groups/20room-upgrade.pl b/tests/53groups/20room-upgrade.pl
new file mode 100644
index 000000000..d1b0ed8fc
--- /dev/null
+++ b/tests/53groups/20room-upgrade.pl
@@ -0,0 +1,110 @@
+# Copyright 2018 New Vector Ltd
+#
+# Licensed under the Apache License, Version 2.0 (the "License");
+# you may not use this file except in compliance with the License.
+# You may obtain a copy of the License at
+#
+#     http://www.apache.org/licenses/LICENSE-2.0
+#
+# Unless required by applicable law or agreed to in writing, software
+# distributed under the License is distributed on an "AS IS" BASIS,
+# WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+# See the License for the specific language governing permissions and
+# limitations under the License.
+
+use Future::Utils qw( repeat );
+use List::Util qw( all first none );
+
+test "Room is transitioned on local and remote groups upon room upgrade",
+   requires => [
+      local_admin_fixture(),
+      remote_admin_fixture(),
+      qw( can_upgrade_room_version )
+   ],
+
+   do => sub {
+      my ( $local_user, $remote_user ) = @_;
+      my ( $room_id, $new_room_id, $local_group_id, $remote_group_id );
+
+      # Create a to-be-upgraded room
+      matrix_create_room_synced(
+         $local_user,
+      )->then( sub {
+         ( $room_id, ) = @_;
+
+         matrix_invite_user_to_room_synced(
+            $local_user, $remote_user, $room_id
+         );
+      })->then( sub {
+         matrix_join_room_synced(
+            $remote_user, $room_id, ( server_name => $local_user->server_name, )
+         );
+      })->then( sub {
+         # Create groups
+         matrix_create_group(
+            $local_user, name => "Local Test Group"
+         );
+      })->then( sub {
+         ( $local_group_id, ) = @_;
+
+         matrix_create_group(
+            $remote_user, name => "Remote Test Group",
+         );
+      })->then( sub {
+         ( $remote_group_id, ) = @_;
+
+         # Add the to-be-upgraded room to groups
+         matrix_add_group_rooms(
+            $local_user, $local_group_id, $room_id
+         );
+      })->then( sub {
+         matrix_add_group_rooms( $remote_user, $remote_group_id, $room_id );
+      })->then( sub {
+         # Upgrade the room
+         upgrade_room_synced(
+            $local_user, $room_id,
+            new_version => $main::TEST_NEW_VERSION,
+         );
+      })->then( sub {
+         ( $new_room_id, ) = @_;
+
+         matrix_invite_user_to_room_synced(
+            $local_user, $remote_user, $new_room_id
+         );
+      })->then( sub {
+         matrix_join_room_synced(
+            $remote_user, $new_room_id, ( server_name => $local_user->server_name, )
+         );
+      })->then( sub{
+         # Check whether the old and new room exist on each group
+         matrix_get_group_rooms( $local_user, $local_group_id );
+      })->then( sub {
+         my ( $body, ) = @_;
+
+         log_if_fail "Old room ID: $room_id, New room ID: $new_room_id";
+         log_if_fail "Rooms on local group", $body;
+
+         assert_json_keys( $body, qw( chunk ) );
+         any { $_->{room_id} eq $new_room_id } @{ $body->{chunk} }
+            or die "Upgraded room not in local group rooms list";
+
+         none { $_->{room_id} eq $room_id } @{ $body->{chunk} }
+            or die "Old room still present in local group rooms list";
+
+         matrix_get_group_rooms( $remote_user, $remote_group_id );
+      })->then( sub {
+         my ( $body, ) = @_;
+
+         log_if_fail "Old room ID: $room_id, New room ID: $new_room_id";
+         log_if_fail "Rooms on remote group", $body;
+
+         assert_json_keys( $body, qw( chunk ) );
+         any { $_->{room_id} eq $new_room_id } @{ $body->{chunk} }
+            or die "Upgraded room not in remote group rooms list";
+
+         none { $_->{room_id} eq $room_id } @{ $body->{chunk} }
+            or die "Old room still present in remote group rooms list";
+
+         Future->done( 1 );
+      });
+   };