diff --git a/osu.Server.QueueProcessor.Tests/BatchProcessorTests.cs b/osu.Server.QueueProcessor.Tests/BatchProcessorTests.cs
index d777fd8..71a4381 100644
--- a/osu.Server.QueueProcessor.Tests/BatchProcessorTests.cs
+++ b/osu.Server.QueueProcessor.Tests/BatchProcessorTests.cs
@@ -195,6 +195,41 @@ public void SendThenErrorDoesRetry()
             Assert.Equal(obj, receivedObject);
         }
 
+        [Fact]
+        public void MultipleErrorsAttachedToCorrectItems()
+        {
+            var cts = new CancellationTokenSource(10000);
+
+            var obj1 = FakeData.New();
+            var obj2 = FakeData.New();
+
+            bool gotCorrectExceptionForItem1 = false;
+            bool gotCorrectExceptionForItem2 = false;
+
+            processor.Error += (exception, item) =>
+            {
+                Assert.NotNull(exception);
+                Assert.Equal(exception, item.Exception);
+
+                gotCorrectExceptionForItem1 |= Equals(item.Data, obj1.Data) && exception.Message == "1";
+                gotCorrectExceptionForItem2 |= Equals(item.Data, obj2.Data) && exception.Message == "2";
+            };
+
+            processor.PushToQueue(new[] { obj1, obj2 });
+
+            processor.Received += o =>
+            {
+                if (Equals(o.Data, obj1.Data)) throw new Exception("1");
+                if (Equals(o.Data, obj2.Data)) throw new Exception("2");
+            };
+
+            processor.Run(cts.Token);
+
+            Assert.Equal(0, processor.GetQueueSize());
+            Assert.True(gotCorrectExceptionForItem1);
+            Assert.True(gotCorrectExceptionForItem2);
+        }
+
         [Fact]
         public void SendThenErrorForeverDoesDrop()
         {
diff --git a/osu.Server.QueueProcessor.Tests/TestBatchProcessor.cs b/osu.Server.QueueProcessor.Tests/TestBatchProcessor.cs
index 63d5cc9..db9c80b 100644
--- a/osu.Server.QueueProcessor.Tests/TestBatchProcessor.cs
+++ b/osu.Server.QueueProcessor.Tests/TestBatchProcessor.cs
@@ -21,7 +21,14 @@ protected override void ProcessResults(IEnumerable<FakeData> items)
         {
             foreach (var item in items)
             {
-                Received?.Invoke(item);
+                try
+                {
+                    Received?.Invoke(item);
+                }
+                catch (Exception e)
+                {
+                    item.Exception = e;
+                }
             }
         }
 
diff --git a/osu.Server.QueueProcessor/QueueItem.cs b/osu.Server.QueueProcessor/QueueItem.cs
index 9e622fb..823a28e 100644
--- a/osu.Server.QueueProcessor/QueueItem.cs
+++ b/osu.Server.QueueProcessor/QueueItem.cs
@@ -12,11 +12,21 @@ namespace osu.Server.QueueProcessor
     [Serializable]
     public abstract class QueueItem
     {
+        [IgnoreDataMember]
+        private bool failed;
+
         /// <summary>
         /// Set to <c>true</c> to mark this item is failed. This will cause it to be retried.
         /// </summary>
         [IgnoreDataMember]
-        public bool Failed { get; set; }
+        public bool Failed
+        {
+            get => failed || Exception != null;
+            set => failed = value;
+        }
+
+        [IgnoreDataMember]
+        public Exception? Exception { get; set; }
 
         /// <summary>
         /// The number of times processing this item has been retried. Handled internally by <see cref="QueueProcessor{T}"/>.
diff --git a/osu.Server.QueueProcessor/QueueProcessor.cs b/osu.Server.QueueProcessor/QueueProcessor.cs
index 8fd2df0..4cfe21c 100644
--- a/osu.Server.QueueProcessor/QueueProcessor.cs
+++ b/osu.Server.QueueProcessor/QueueProcessor.cs
@@ -132,11 +132,11 @@ public void Run(CancellationToken cancellation = default)
 
                             // individual processing should not be cancelled as we have already grabbed from the queue.
                             Task.Factory.StartNew(() => { ProcessResults(items); }, CancellationToken.None, TaskCreationOptions.HideScheduler, threadPool)
-                                .ContinueWith(t =>
+                                .ContinueWith(_ =>
                                 {
                                     foreach (var item in items)
                                     {
-                                        if (t.Exception != null || item.Failed)
+                                        if (item.Failed)
                                         {
                                             Interlocked.Increment(ref totalErrors);
 
@@ -145,12 +145,18 @@ public void Run(CancellationToken cancellation = default)
 
                                             Interlocked.Increment(ref consecutiveErrors);
 
-                                            Error?.Invoke(t.Exception, item);
+                                            try
+                                            {
+                                                Error?.Invoke(item.Exception, item);
+                                            }
+                                            catch
+                                            {
+                                            }
 
-                                            if (t.Exception != null)
-                                                SentrySdk.CaptureException(t.Exception);
+                                            if (item.Exception != null)
+                                                SentrySdk.CaptureException(item.Exception);
 
-                                            Console.WriteLine($"Error processing {item}: {t.Exception}");
+                                            Console.WriteLine($"Error processing {item}: {item.Exception}");
                                             attemptRetry(item);
                                         }
                                         else
@@ -197,8 +203,6 @@ private void setupSentry(SentryOptions options)
 
         private void attemptRetry(T item)
         {
-            item.Failed = false;
-
             if (item.TotalRetries++ < config.MaxRetries)
             {
                 Console.WriteLine($"Re-queueing for attempt {item.TotalRetries} / {config.MaxRetries}");
@@ -274,11 +278,26 @@ protected virtual void ProcessResult(T item)
         /// <summary>
         /// Implement to process batches of items from the queue.
         /// </summary>
+        /// <remarks>
+        /// In most cases, you should only need to override and implement <see cref="ProcessResult"/>.
+        /// Only override this if you need more efficient batch processing.
+        ///
+        /// If overriding this method, you should try-catch for exceptions, and set any exception against
+        /// the relevant <see cref="QueueItem"/>. If this is not done, failures will not be handled correctly.</remarks>
         /// <param name="items">The items to process.</param>
         protected virtual void ProcessResults(IEnumerable<T> items)
         {
             foreach (var item in items)
-                ProcessResult(item);
+            {
+                try
+                {
+                    ProcessResult(item);
+                }
+                catch (Exception e)
+                {
+                    item.Exception = e;
+                }
+            }
         }
     }
 }