diff --git a/MediaBrowser.Api/Sync/SyncService.cs b/MediaBrowser.Api/Sync/SyncService.cs
index 5863e05e3..593c3a108 100644
--- a/MediaBrowser.Api/Sync/SyncService.cs
+++ b/MediaBrowser.Api/Sync/SyncService.cs
@@ -244,7 +244,15 @@ namespace MediaBrowser.Api.Sync
             var task = _syncManager.ReportSyncJobItemTransferBeginning(request.Id);
             Task.WaitAll(task);
 
-            return ToStaticFileResult(jobItem.OutputPath);
+            return ResultFactory.GetStaticFileResult(Request, new StaticFileResultOptions
+            {
+                Path = jobItem.OutputPath,
+                OnError = () =>
+                {
+                    var failedTask = _syncManager.ReportSyncJobItemTransferFailed(request.Id);
+                    Task.WaitAll(failedTask);
+                }
+            });
         }
 
         public object Get(GetSyncDialogOptions request)
diff --git a/MediaBrowser.Controller/Net/StaticResultOptions.cs b/MediaBrowser.Controller/Net/StaticResultOptions.cs
index 6a104554a..b5efc1b8f 100644
--- a/MediaBrowser.Controller/Net/StaticResultOptions.cs
+++ b/MediaBrowser.Controller/Net/StaticResultOptions.cs
@@ -19,6 +19,7 @@ namespace MediaBrowser.Controller.Net
         public IDictionary<string, string> ResponseHeaders { get; set; }
 
         public Action OnComplete { get; set; }
+        public Action OnError { get; set; }
 
         public StaticResultOptions()
         {
diff --git a/MediaBrowser.Server.Implementations/HttpServer/HttpResultFactory.cs b/MediaBrowser.Server.Implementations/HttpServer/HttpResultFactory.cs
index 961d58eb6..9dc8d94e2 100644
--- a/MediaBrowser.Server.Implementations/HttpServer/HttpResultFactory.cs
+++ b/MediaBrowser.Server.Implementations/HttpServer/HttpResultFactory.cs
@@ -476,7 +476,8 @@ namespace MediaBrowser.Server.Implementations.HttpServer
 
                 return new StreamWriter(stream, contentType, _logger)
                 {
-                    OnComplete = options.OnComplete
+                    OnComplete = options.OnComplete,
+                    OnError = options.OnError
                 };
             }
 
diff --git a/MediaBrowser.Server.Implementations/HttpServer/StreamWriter.cs b/MediaBrowser.Server.Implementations/HttpServer/StreamWriter.cs
index daa5b86d9..a756f4aa8 100644
--- a/MediaBrowser.Server.Implementations/HttpServer/StreamWriter.cs
+++ b/MediaBrowser.Server.Implementations/HttpServer/StreamWriter.cs
@@ -36,6 +36,7 @@ namespace MediaBrowser.Server.Implementations.HttpServer
         }
 
         public Action OnComplete { get; set; }
+        public Action OnError { get; set; }
 
         /// <summary>
         /// Initializes a new instance of the <see cref="StreamWriter" /> class.
@@ -102,6 +103,11 @@ namespace MediaBrowser.Server.Implementations.HttpServer
             {
                 Logger.ErrorException("Error streaming data", ex);
 
+                if (OnError != null)
+                {
+                    OnError();
+                }
+                
                 throw;
             }
             finally