diff --git a/osu.Game.Tests/Visual/Menus/TestSceneMainMenu.cs b/osu.Game.Tests/Visual/Menus/TestSceneMainMenu.cs
index 613d8347b7..aab3716463 100644
--- a/osu.Game.Tests/Visual/Menus/TestSceneMainMenu.cs
+++ b/osu.Game.Tests/Visual/Menus/TestSceneMainMenu.cs
@@ -48,6 +48,7 @@ namespace osu.Game.Tests.Visual.Menus
                             {
                                 new PlaylistItem(beatmap)
                             },
+                            StartDate = { Value = DateTimeOffset.Now.AddMinutes(-30) },
                             EndDate = { Value = DateTimeOffset.Now.AddSeconds(60) }
                         });
                         return true;
diff --git a/osu.Game.Tests/Visual/UserInterface/TestSceneMainMenuButton.cs b/osu.Game.Tests/Visual/UserInterface/TestSceneMainMenuButton.cs
index af98aa21db..98f2b129ff 100644
--- a/osu.Game.Tests/Visual/UserInterface/TestSceneMainMenuButton.cs
+++ b/osu.Game.Tests/Visual/UserInterface/TestSceneMainMenuButton.cs
@@ -58,6 +58,7 @@ namespace osu.Game.Tests.Visual.UserInterface
                             {
                                 new PlaylistItem(beatmap)
                             },
+                            StartDate = { Value = DateTimeOffset.Now.AddMinutes(-5) },
                             EndDate = { Value = DateTimeOffset.Now.AddSeconds(30) }
                         });
                         return true;
@@ -95,8 +96,13 @@ namespace osu.Game.Tests.Visual.UserInterface
                     },
                 };
             });
-            AddAssert("no notification posted", () => notificationOverlay.AllNotifications.Count(), () => Is.Zero);
+            AddAssert("notification posted", () => notificationOverlay.AllNotifications.Count(), () => Is.EqualTo(1));
 
+            AddStep("clear notifications", () =>
+            {
+                foreach (var notification in notificationOverlay.AllNotifications)
+                    notification.Close(runFlingAnimation: false);
+            });
             AddStep("beatmap of the day not active", () => metadataClient.DailyChallengeUpdated(null));
             AddAssert("no notification posted", () => notificationOverlay.AllNotifications.Count(), () => Is.Zero);
 
@@ -105,7 +111,7 @@ namespace osu.Game.Tests.Visual.UserInterface
             {
                 RoomID = 1234,
             }));
-            AddAssert("notification posted", () => notificationOverlay.AllNotifications.Count(), () => Is.EqualTo(1));
+            AddAssert("no notification posted", () => notificationOverlay.AllNotifications.Count(), () => Is.Zero);
         }
     }
 }
diff --git a/osu.Game/Screens/Menu/DailyChallengeButton.cs b/osu.Game/Screens/Menu/DailyChallengeButton.cs
index ac04afdc4d..2357c60f3d 100644
--- a/osu.Game/Screens/Menu/DailyChallengeButton.cs
+++ b/osu.Game/Screens/Menu/DailyChallengeButton.cs
@@ -154,7 +154,9 @@ namespace osu.Game.Screens.Menu
                     cover.OnlineInfo = TooltipContent = room.Playlist.FirstOrDefault()?.Beatmap.BeatmapSet as APIBeatmapSet;
 
                     // We only want to notify the user if a new challenge recently went live.
-                    if (Math.Abs((DateTimeOffset.Now - room.StartDate.Value!.Value).TotalSeconds) < 600 && room.RoomID.Value != lastNotifiedDailyChallengeRoomId)
+                    if (room.StartDate.Value != null
+                        && Math.Abs((DateTimeOffset.Now - room.StartDate.Value!.Value).TotalSeconds) < 600
+                        && room.RoomID.Value != lastNotifiedDailyChallengeRoomId)
                     {
                         lastNotifiedDailyChallengeRoomId = room.RoomID.Value;
                         notificationOverlay?.Post(new NewDailyChallengeNotification(room));