diff --git a/tests/30rooms/60version_upgrade.pl b/tests/30rooms/60version_upgrade.pl
index b415479aa..fc0c2f855 100644
--- a/tests/30rooms/60version_upgrade.pl
+++ b/tests/30rooms/60version_upgrade.pl
@@ -15,6 +15,8 @@
 use Future::Utils qw( repeat );
 use List::Util qw( all first );
 
+push our @EXPORT, qw ( upgrade_room_synced $TEST_NEW_VERSION );
+
 # TODO: switch this to '2' once that is released
 my $TEST_NEW_VERSION = 'vdh-test-version';
 
@@ -59,6 +61,43 @@ sub upgrade_room {
    });
 }
 
+=head2 is_direct_room
+
+    is_direct_room( $user, $room_id )->then( sub {
+        my ( $is_direct ) = @_;
+    })
+
+Check if a room ID is considered to be a direct chat by the given user.
+
+=cut
+
+sub is_direct_room {
+   my ( $user, $room_id ) = @_;
+
+   # Download account data events from sync
+   matrix_get_account_data( $user, "m.direct" )->then( sub {
+      # Should only have the m.direct event in account_data
+      my ( $data ) = @_;
+
+      log_if_fail "m.direct account data", $data;
+
+      # Check if the room_id is in the list of direct rooms
+      foreach my $user_id ( keys %{ $data } ) {
+         my $room_ids = $data->{$user_id};
+
+         # Return whether the given room ID is in the response
+         foreach my $room (@$room_ids) {
+            if ( $room eq $room_id ) {
+               return Future->done( 1 );
+            }
+         }
+      }
+
+      # Didn't find a direct room with our room ID
+      Future->done( 0 );
+   });
+}
+
 =head2 upgrade_room_synced
 
     upgrade_room_synced( $user, $room_id, %opts )->then( sub {
@@ -474,6 +513,39 @@ sub upgrade_room_synced {
       });
    };
 
+test "/upgrade preserves direct room state",
+   requires => [
+      local_user_and_room_fixtures(),
+      qw( can_upgrade_room_version ),
+   ],
+
+   do => sub {
+      my ( $creator, $room_id ) = @_;
+
+      my $new_room_id;
+      my $user_id = $creator->user_id;
+
+      do_request_json_for(
+         $creator,
+         method => "PUT",
+         uri    => "/r0/user/$user_id/account_data/m.direct",
+         content => { $user_id => [$room_id] },
+      )->then( sub {
+         upgrade_room_synced(
+            $creator, $room_id,
+            new_version => $TEST_NEW_VERSION,
+         );
+      })->then( sub {
+         ( $new_room_id ) = @_;
+
+         is_direct_room( $creator, $new_room_id );
+      })->then( sub {
+         my ( $is_direct_room ) = @_;
+
+         $is_direct_room == 1 or die "Expected upgraded room to be a direct room";
+         Future->done( 1 );
+      });
+   };
 
 test "/upgrade restricts power levels in the old room",
    requires => [
diff --git a/tests/42tags.pl b/tests/42tags.pl
index e7df893b0..572081245 100644
--- a/tests/42tags.pl
+++ b/tests/42tags.pl
@@ -407,3 +407,44 @@ sub check_account_data {
          Future->done( 1 );
       });
    };
+
+test "/upgrade copies user tags to the new room",
+   requires => [
+      local_user_and_room_fixtures(),
+      qw( can_upgrade_room_version can_add_tag ),
+   ],
+
+   do => sub {
+      my ( $user, $room_id ) = @_;
+      my ( $new_room_id );
+
+      matrix_add_tag(
+         $user, $room_id, "test_tag", {}
+      )->then( sub {
+         matrix_sync( $user );
+      })->then( sub {
+         upgrade_room_synced(
+            $user, $room_id,
+            new_version => $main::TEST_NEW_VERSION,
+         );
+      })->then( sub {
+         ( $new_room_id, ) = @_;
+
+         matrix_sync_again( $user );
+      })->then( sub {
+         my ( $sync_body ) = @_;
+
+         log_if_fail "sync body", $sync_body;
+
+         my $room = $sync_body->{rooms}{join}{$new_room_id};
+
+         matrix_list_tags( $user, $new_room_id );
+      })->then( sub {
+         my ( $tags ) = @_;
+
+         keys %{ $tags } == 1 or die "Expected one tag in the upgraded room";
+         defined $tags->{test_tag} or die "Unexpected tag";
+
+         Future->done(1);
+      });
+   };