diff --git a/osu.Game/Screens/OnlinePlay/Components/ReadyButton.cs b/osu.Game/Screens/OnlinePlay/Components/ReadyButton.cs
index 8f85608b29..5a4a0a0fba 100644
--- a/osu.Game/Screens/OnlinePlay/Components/ReadyButton.cs
+++ b/osu.Game/Screens/OnlinePlay/Components/ReadyButton.cs
@@ -3,13 +3,15 @@
 
 using osu.Framework.Allocation;
 using osu.Framework.Bindables;
+using osu.Framework.Graphics.Cursor;
+using osu.Framework.Localisation;
 using osu.Game.Graphics.UserInterface;
 using osu.Game.Online;
 using osu.Game.Online.Rooms;
 
 namespace osu.Game.Screens.OnlinePlay.Components
 {
-    public abstract class ReadyButton : TriangleButton
+    public abstract class ReadyButton : TriangleButton, IHasTooltip
     {
         public new readonly BindableBool Enabled = new BindableBool();
 
@@ -24,6 +26,18 @@ namespace osu.Game.Screens.OnlinePlay.Components
             Enabled.BindValueChanged(_ => updateState(), true);
         }
 
-        private void updateState() => base.Enabled.Value = availability.Value.State == DownloadState.LocallyAvailable && Enabled.Value;
+        private void updateState() =>
+            base.Enabled.Value = availability.Value.State == DownloadState.LocallyAvailable && Enabled.Value;
+
+        public virtual LocalisableString TooltipText
+        {
+            get
+            {
+                if (Enabled.Value)
+                    return string.Empty;
+
+                return "Beatmap not downloaded";
+            }
+        }
     }
 }
diff --git a/osu.Game/Screens/OnlinePlay/Components/RoomLocalUserInfo.cs b/osu.Game/Screens/OnlinePlay/Components/RoomLocalUserInfo.cs
index 1fcf7f2277..3bad6cb183 100644
--- a/osu.Game/Screens/OnlinePlay/Components/RoomLocalUserInfo.cs
+++ b/osu.Game/Screens/OnlinePlay/Components/RoomLocalUserInfo.cs
@@ -14,6 +14,9 @@ namespace osu.Game.Screens.OnlinePlay.Components
     {
         private OsuSpriteText attemptDisplay;
 
+        [Resolved]
+        private OsuColour colours { get; set; }
+
         public RoomLocalUserInfo()
         {
             AutoSizeAxes = Axes.Both;
@@ -54,6 +57,9 @@ namespace osu.Game.Screens.OnlinePlay.Components
                 {
                     int remaining = MaxAttempts.Value.Value - UserScore.Value.PlaylistItemAttempts.Sum(a => a.Attempts);
                     attemptDisplay.Text += $" ({remaining} remaining)";
+
+                    if (remaining == 0)
+                        attemptDisplay.Colour = colours.RedLight;
                 }
             }
             else
diff --git a/osu.Game/Screens/OnlinePlay/Playlists/PlaylistsReadyButton.cs b/osu.Game/Screens/OnlinePlay/Playlists/PlaylistsReadyButton.cs
index 9ac1fe1722..24f112ef0c 100644
--- a/osu.Game/Screens/OnlinePlay/Playlists/PlaylistsReadyButton.cs
+++ b/osu.Game/Screens/OnlinePlay/Playlists/PlaylistsReadyButton.cs
@@ -2,8 +2,10 @@
 // See the LICENCE file in the repository root for full licence text.
 
 using System;
+using System.Linq;
 using osu.Framework.Allocation;
 using osu.Framework.Bindables;
+using osu.Framework.Localisation;
 using osu.Game.Beatmaps;
 using osu.Game.Graphics;
 using osu.Game.Online.Rooms;
@@ -16,6 +18,12 @@ namespace osu.Game.Screens.OnlinePlay.Playlists
         [Resolved(typeof(Room), nameof(Room.EndDate))]
         private Bindable<DateTimeOffset?> endDate { get; set; }
 
+        [Resolved(typeof(Room), nameof(Room.MaxAttempts))]
+        private Bindable<int?> maxAttempts { get; set; }
+
+        [Resolved(typeof(Room), nameof(Room.UserScore))]
+        private Bindable<PlaylistAggregateScore> userScore { get; set; }
+
         [Resolved]
         private IBindable<WorkingBeatmap> gameBeatmap { get; set; }
 
@@ -32,11 +40,49 @@ namespace osu.Game.Screens.OnlinePlay.Playlists
             Triangles.ColourLight = colours.GreenLight;
         }
 
+        private bool hasRemainingAttempts = true;
+
+        protected override void LoadComplete()
+        {
+            base.LoadComplete();
+
+            userScore.BindValueChanged(aggregate =>
+            {
+                if (maxAttempts.Value == null)
+                    return;
+
+                int remaining = maxAttempts.Value.Value - aggregate.NewValue.PlaylistItemAttempts.Sum(a => a.Attempts);
+
+                hasRemainingAttempts = remaining > 0;
+            });
+        }
+
         protected override void Update()
         {
             base.Update();
 
-            Enabled.Value = endDate.Value != null && DateTimeOffset.UtcNow.AddSeconds(30).AddMilliseconds(gameBeatmap.Value.Track.Length) < endDate.Value;
+            Enabled.Value = hasRemainingAttempts && enoughTimeLeft;
         }
+
+        public override LocalisableString TooltipText
+        {
+            get
+            {
+                if (Enabled.Value)
+                    return string.Empty;
+
+                if (!enoughTimeLeft)
+                    return "No time left!";
+
+                if (!hasRemainingAttempts)
+                    return "Attempts exhausted!";
+
+                return base.TooltipText;
+            }
+        }
+
+        private bool enoughTimeLeft =>
+            // This should probably consider the length of the currently selected item, rather than a constant 30 seconds.
+            endDate.Value != null && DateTimeOffset.UtcNow.AddSeconds(30).AddMilliseconds(gameBeatmap.Value.Track.Length) < endDate.Value;
     }
 }
diff --git a/osu.Game/Screens/OnlinePlay/Playlists/PlaylistsRoomSubScreen.cs b/osu.Game/Screens/OnlinePlay/Playlists/PlaylistsRoomSubScreen.cs
index d5e423a438..6d2a426e70 100644
--- a/osu.Game/Screens/OnlinePlay/Playlists/PlaylistsRoomSubScreen.cs
+++ b/osu.Game/Screens/OnlinePlay/Playlists/PlaylistsRoomSubScreen.cs
@@ -37,6 +37,8 @@ namespace osu.Game.Screens.OnlinePlay.Playlists
         private MatchLeaderboard leaderboard;
         private SelectionPollingComponent selectionPollingComponent;
 
+        private FillFlowContainer progressSection;
+
         public PlaylistsRoomSubScreen(Room room)
             : base(room, false) // Editing is temporarily not allowed.
         {
@@ -67,6 +69,8 @@ namespace osu.Game.Screens.OnlinePlay.Playlists
                     Schedule(() => SelectedItem.Value = Room.Playlist.FirstOrDefault());
                 }
             }, true);
+
+            Room.MaxAttempts.BindValueChanged(attempts => progressSection.Alpha = Room.MaxAttempts.Value != null ? 1 : 0, true);
         }
 
         protected override Drawable CreateMainContent() => new GridContainer
@@ -153,6 +157,22 @@ namespace osu.Game.Screens.OnlinePlay.Playlists
                                 },
                             },
                             new Drawable[]
+                            {
+                                progressSection = new FillFlowContainer
+                                {
+                                    RelativeSizeAxes = Axes.X,
+                                    AutoSizeAxes = Axes.Y,
+                                    Alpha = 0,
+                                    Margin = new MarginPadding { Bottom = 10 },
+                                    Direction = FillDirection.Vertical,
+                                    Children = new Drawable[]
+                                    {
+                                        new OverlinedHeader("Progress"),
+                                        new RoomLocalUserInfo(),
+                                    }
+                                },
+                            },
+                            new Drawable[]
                             {
                                 new OverlinedHeader("Leaderboard")
                             },
@@ -162,6 +182,7 @@ namespace osu.Game.Screens.OnlinePlay.Playlists
                         },
                         RowDimensions = new[]
                         {
+                            new Dimension(GridSizeMode.AutoSize),
                             new Dimension(GridSizeMode.AutoSize),
                             new Dimension(GridSizeMode.AutoSize),
                             new Dimension(),