diff --git a/osu.Game/Online/HubClientConnector.cs b/osu.Game/Online/HubClientConnector.cs
index 5c11eed381..261724e315 100644
--- a/osu.Game/Online/HubClientConnector.cs
+++ b/osu.Game/Online/HubClientConnector.cs
@@ -20,6 +20,8 @@ namespace osu.Game.Online
 {
     public class HubClientConnector : IHubClientConnector
     {
+        public const string SERVER_SHUTDOWN_MESSAGE = "Server is shutting down.";
+
         /// <summary>
         /// Invoked whenever a new hub connection is built, to configure it before it's started.
         /// </summary>
diff --git a/osu.Game/Online/Multiplayer/MultiplayerClientExtensions.cs b/osu.Game/Online/Multiplayer/MultiplayerClientExtensions.cs
index 4729765084..cda313bd0a 100644
--- a/osu.Game/Online/Multiplayer/MultiplayerClientExtensions.cs
+++ b/osu.Game/Online/Multiplayer/MultiplayerClientExtensions.cs
@@ -25,12 +25,7 @@ namespace osu.Game.Online.Multiplayer
 
                     Debug.Assert(exception != null);
 
-                    string message = exception is HubException
-                        // HubExceptions arrive with additional message context added, but we want to display the human readable message:
-                        // "An unexpected error occurred invoking 'AddPlaylistItem' on the server.InvalidStateException: Can't enqueue more than 3 items at once."
-                        // We generally use the message field for a user-parseable error (eventually to be replaced), so drop the first part for now.
-                        ? exception.Message.Substring(exception.Message.IndexOf(':') + 1).Trim()
-                        : exception.Message;
+                    string message = exception.GetHubExceptionMessage() ?? exception.Message;
 
                     Logger.Log(message, level: LogLevel.Important);
                     onError?.Invoke(exception);
@@ -40,5 +35,16 @@ namespace osu.Game.Online.Multiplayer
                     onSuccess?.Invoke();
                 }
             });
+
+        public static string? GetHubExceptionMessage(this Exception exception)
+        {
+            if (exception is HubException hubException)
+                // HubExceptions arrive with additional message context added, but we want to display the human readable message:
+                // "An unexpected error occurred invoking 'AddPlaylistItem' on the server.InvalidStateException: Can't enqueue more than 3 items at once."
+                // We generally use the message field for a user-parseable error (eventually to be replaced), so drop the first part for now.
+                return hubException.Message.Substring(exception.Message.IndexOf(':') + 1).Trim();
+
+            return null;
+        }
     }
 }
diff --git a/osu.Game/Online/Multiplayer/OnlineMultiplayerClient.cs b/osu.Game/Online/Multiplayer/OnlineMultiplayerClient.cs
index 4dc23d8b85..a3423d4189 100644
--- a/osu.Game/Online/Multiplayer/OnlineMultiplayerClient.cs
+++ b/osu.Game/Online/Multiplayer/OnlineMultiplayerClient.cs
@@ -3,10 +3,12 @@
 
 #nullable enable
 
+using System;
 using System.Collections.Generic;
 using System.Diagnostics;
 using System.Threading;
 using System.Threading.Tasks;
+using Microsoft.AspNetCore.SignalR;
 using Microsoft.AspNetCore.SignalR.Client;
 using osu.Framework.Allocation;
 using osu.Framework.Bindables;
@@ -71,14 +73,23 @@ namespace osu.Game.Online.Multiplayer
             }
         }
 
-        protected override Task<MultiplayerRoom> JoinRoom(long roomId, string? password = null)
+        protected override async Task<MultiplayerRoom> JoinRoom(long roomId, string? password = null)
         {
             if (!IsConnected.Value)
-                return Task.FromCanceled<MultiplayerRoom>(new CancellationToken(true));
+                throw new OperationCanceledException();
 
             Debug.Assert(connection != null);
 
-            return connection.InvokeAsync<MultiplayerRoom>(nameof(IMultiplayerServer.JoinRoomWithPassword), roomId, password ?? string.Empty);
+            try
+            {
+                return await connection.InvokeAsync<MultiplayerRoom>(nameof(IMultiplayerServer.JoinRoomWithPassword), roomId, password ?? string.Empty);
+            }
+            catch (HubException exception)
+            {
+                if (exception.GetHubExceptionMessage() == HubClientConnector.SERVER_SHUTDOWN_MESSAGE)
+                    connector?.Reconnect();
+                throw;
+            }
         }
 
         protected override Task LeaveRoomInternal()
diff --git a/osu.Game/Online/Spectator/OnlineSpectatorClient.cs b/osu.Game/Online/Spectator/OnlineSpectatorClient.cs
index 4d6ca0b311..0f77f723db 100644
--- a/osu.Game/Online/Spectator/OnlineSpectatorClient.cs
+++ b/osu.Game/Online/Spectator/OnlineSpectatorClient.cs
@@ -5,10 +5,12 @@
 
 using System.Diagnostics;
 using System.Threading.Tasks;
+using Microsoft.AspNetCore.SignalR;
 using Microsoft.AspNetCore.SignalR.Client;
 using osu.Framework.Allocation;
 using osu.Framework.Bindables;
 using osu.Game.Online.API;
+using osu.Game.Online.Multiplayer;
 
 namespace osu.Game.Online.Spectator
 {
@@ -47,14 +49,23 @@ namespace osu.Game.Online.Spectator
             }
         }
 
-        protected override Task BeginPlayingInternal(SpectatorState state)
+        protected override async Task BeginPlayingInternal(SpectatorState state)
         {
             if (!IsConnected.Value)
-                return Task.CompletedTask;
+                return;
 
             Debug.Assert(connection != null);
 
-            return connection.SendAsync(nameof(ISpectatorServer.BeginPlaySession), state);
+            try
+            {
+                await connection.SendAsync(nameof(ISpectatorServer.BeginPlaySession), state);
+            }
+            catch (HubException exception)
+            {
+                if (exception.GetHubExceptionMessage() == HubClientConnector.SERVER_SHUTDOWN_MESSAGE)
+                    connector?.Reconnect();
+                throw;
+            }
         }
 
         protected override Task SendFramesInternal(FrameDataBundle bundle)