diff --git a/osu.Game.Tests/Visual/Online/TestSceneCurrentlyOnlineDisplay.cs b/osu.Game.Tests/Visual/Online/TestSceneCurrentlyOnlineDisplay.cs
index 7687cd195d..b696c5d8ca 100644
--- a/osu.Game.Tests/Visual/Online/TestSceneCurrentlyOnlineDisplay.cs
+++ b/osu.Game.Tests/Visual/Online/TestSceneCurrentlyOnlineDisplay.cs
@@ -81,6 +81,21 @@ namespace osu.Game.Tests.Visual.Online
             AddStep("End watching user presence", () => metadataClient.EndWatchingUserPresence());
         }
 
+        [Test]
+        public void TestUserWasPlayingBeforeWatchingUserPresence()
+        {
+            AddStep("User began playing", () => spectatorClient.SendStartPlay(streamingUser.Id, 0));
+            AddStep("Begin watching user presence", () => metadataClient.BeginWatchingUserPresence());
+            AddStep("Add online user", () => metadataClient.UserPresenceUpdated(streamingUser.Id, new UserPresence { Status = UserStatus.Online, Activity = new UserActivity.ChoosingBeatmap() }));
+            AddUntilStep("Panel loaded", () => currentlyOnline.ChildrenOfType<UserGridPanel>().FirstOrDefault()?.User.Id == 2);
+            AddAssert("Spectate button enabled", () => currentlyOnline.ChildrenOfType<PurpleRoundedButton>().First().Enabled.Value, () => Is.True);
+
+            AddStep("User finished playing", () => spectatorClient.SendEndPlay(streamingUser.Id));
+            AddAssert("Spectate button disabled", () => currentlyOnline.ChildrenOfType<PurpleRoundedButton>().First().Enabled.Value, () => Is.False);
+            AddStep("Remove playing user", () => metadataClient.UserPresenceUpdated(streamingUser.Id, null));
+            AddStep("End watching user presence", () => metadataClient.EndWatchingUserPresence());
+        }
+
         internal partial class TestUserLookupCache : UserLookupCache
         {
             private static readonly string[] usernames =